TITLE OF THE INVENTION

Phenyl alkyl carbamate derivative compound and pharmaceutical composition containing the same

BACKGROUND OF THE INVENTION

(a) Field of the Invention

A phenyl alkyl carbamate derivative compound and a pharmaceutical composition containing the compound are provided. More specifically, the present invention relates to phenyl alkyl carbamate derivative compounds and a pharmaceutically acceptable salt thereof, which have a considerably high muscle relaxation effect and low toxicity, and compositions for muscle relaxation containing the compounds and/or pharmaceutically acceptable salt thereof as an active ingredient.

(b) Description of the Related Art

The central nervous system(CNS) disorders nowadays concern large sections of the population. In particular on account of the increase in elderly people, the numbers of patients are increasing continuously.

Myotony, or spasm, is one of skeletal muscle dysfunction diseases due to increase of muscle tone, and caused by central nervous system damage due to various causes such as external injury, and the like. The muscle tension is caused by various causes, for example, fatigue, age-related spine deformity, and the like, and causes spasticity in skeletal muscles of the neck, shoulders, arms, waist, and back; spastic paralysis causing disability of voluntary movement due to muscle hypertonia of hands and feet by disorder of central nervous system and a combination thereof, thereby resulting in serious hindrances to normal life.

In particular, spastic paralysis is a serious disorder with accompanying symptoms including muscle tension and/or muscle stiffmess of hands and feet, difficulty in walking, and the like, thererby causing serious hindrances to normal life. Centrally acting muscle relaxants relieve muscle tension by blocking receptors associated with stimulating muscular function or stimulating receptors associated with inhibiting muscular function, or reducing excessively activated reflex function.

Such centrally acting muscle relaxants may include Methocarbaamol, Chlormezanon,

Carisoprodol, Eperisone, Phenprobamide, and the like. However, these drugs act on interneuron of the spinal cord, thereby inhibiting monosynaptic and polysynaptic reflexes, and thus, may cause side effects, such as central nervous inhibition, muscle weakness, and the like.

US Patent No. 3,313,692 discloses a racemic carbamate compound useful as a therapeutic agent for the central nervous system with decreased side effects compared to cholinergic agent. US Patent Nos. 2,884,444, 2,937,119, and 3,265,727 suggest dicarbamate compounds useful as therapeutic agents for central nervous system disorders, and US Patent No. 2,937,119 discloses a N-isopropyl-2 -methyl -2 -propyl- 1,3 -propanediol dicarbamate, which was released with the trademark of Soma as a muscle relaxant.

Muscle relaxants are used for improving various symptoms, such as vascular disorders of the spinal cord, spastic spinal paralysis, cervical spondylosis, cerebral palsy, sequelae of injuries (spinal cord injuries, head injuries), spinocerebellar degeneration, and the like, which are associated with muscle spasm involved in musculoskeletal diseases, and also used as an adjuvant to anesthestic agent.

Considering the various and valuable uses of muscle relaxants as aforementioned, development of more effective muscel relaxant is needed.

SUMMARY OF THE INVENTION

An embodiment of the present invention provides a phenyl alkyl carbamate derivative compound represented by Chemical Formula 1; a racemate, an enantiomer, a diastereomer, a mixture of enantiomers, or a mixture of diastereomers thereof; or a pharmaceutically acceptable salt thereof:

[Chemical Formula 1

wherein,

X is a halogen, for example, chlorine, fluorine, iodine, or bromine,

n, that means the number of substituent X, is an integer from 1 to 5, for example, 1 or 2, l is a hydrogen or C1-C4 linear or branched alkyl group, for example, methyl group, ethyl group, isopropyl group, or butyl group, A is selected from the group consisting of hydrogen, a C1-C4 linear or branched alkyl group (such as a methyl group, etc.), a C2-C4 alkoxy alky ether group (such as a methoxy

methyl group (MOM), etc.), and a carbamoyl derivative represented by ,

B is selected from the group consisting of hydrogen, a C1-C4 linear or branched alkyl roup (such as a methyl group, etc.), a C2-C4 alkoxy alky ether group (such as a methoxy

R2 and R3 may be the same as or different from each other, and independently selected from the group consisting of hydrogen, a linear or branched alkyl group of C1-C4, for example C1-C3, a cycloalkyl group of C3-C8, for example C3-C7, and benzyl group, and more specifically, R2 and R3 may be the same as or different from each other, and independently selected from the group consisting of hydrogen, methyl group, propyl group, isopropyl group, cyclopropyl group, cyclohexyl group, bicycloheptane group, and benzyl group.

In a concrete embodiment, when one of A and B is hydrogen, the other is neither hydrogen nor the carbamoyl derivative.

Another embodiment provides a pharmaceutical composition containing a phenyl alkyl carbamate derivertive compound represented by Chemical Formula 1 ; a racemate, an enantiomer, a diastereomer, a mixture of enantiomers, or a mixture of diastereomers thereof; or a pharmaceutically acceptable salt thereof, as an active ingredient.

Another embodiment provides a pharmaceutical composition for muscle relaxation, or treating and/or preventing a muscle spasm associated disease, containing a phenyl alkyl carbamate derivative compound represented by Chemical Formula 1 ; a racemate, an enantiomer, a diastereomer, a mixture of enantiomers, or a mixture of diastereomers thereof; or a pharmaceutically acceptable salt thereof, as an active ingredient.

Another embodiment provides a method of muscle relaxation, or treating and/or preventing a muscle spasm associated disease, comprising administering a therapeutically effective amount of a phenyl alkyl carbamate derivative compound represented by Chemical Formula 1 ; a racemate, an enantiomer, a diastereomer, a mixture of enantiomers, or a mixture of diastereomers thereof; or a pharmaceutically acceptable salt thereof, to a subject in need of muscle relaxation.

Another embodiment provides a phenyl alkyl carbamate derivative compound represented by Chemical Formula 1; a racemate, an enantiomer, a diastereomer, a mixture of enantiomers, or a mixture of diastereomers thereof; or a pharmaceutically acceptable salt thereof, a for use in muscle relaxation.

Another embodiment provides a use of phenyl alkyl carbamate derivative compound represented by Chemical Formula 1; a racemate, an enantiomer, a diastereomer, a mixture of enantiomers, or a mixture of diastereomers thereof; or a pharmaceutically acceptable salt thereof, in muscle relaxation or in preparing a muscle relaxant.

DETAILED DESCRIPTION OF THE EMBODIMENTS

Upon attempting to discover a muscle relaxant with more excellent efficacy and decreased side effects, the present inventors found that substituted phenyl alkyl carbamate derivative compounds represented by the following Chemical Formula 1 exhibit a considerably excellent activity of muscle relaxation with very low toxicity, to complete the present invention.

Therefore, an embodiment provides a phenyl alkyl carbamate derivative compound represented by the following Chemical Formula 1 :

[Chemical Formula 1

wherein,

X is a halogen, for example, chlorine, fluorine, iodine, or bromine,

n, that means the number of substituent X, is an integer from 1 to 5, for example, 1 or 2,

Rl is a hydrogen or C1-C4 linear or branched alkyl group, for example, methyl group, ethyl group, isopropyl group, or butyl group,

A is selected from the group consisting of hydrogen, a C1-C4 linear or branched alkyl group (such as a methyl group, etc.), a C2-C4 alkoxy alky ether group (such as a methoxy methyl group (MOM), etc.), and a carbamoyl derivative represented by ,

B is selected from the group consisting of hydrogen, a C1-C4 linear or branched alkyl group (such as a methyl group, etc.), a C2-C4 alkoxy alky ether group (such as a methoxy

H methyl group (MOM), etc.), and a carbamoyl derivative represented by 0 , and

R2 and R3 may be the same as or different from each other, and independently selected from the group consisting of hydrogen, a linear or branched alkyl group of C1-C4, for example C1-C3, a cycloalkyl group of C3-C8, for example C3-C7, and benzyl group, and more specifically, R2 and R3 may be the same as or different from each other, and independently selected from the group consisting of hydrogen, methyl group, propyl group, isopropyl group, cyclopropyl group, cyclohexyl group, bicycloheptane group, and benzyl group.

In a concrete embodiment, when one of A and B is hydrogen, the other is neither hydrogen nor the carbamoyl derivative.

In a concrete embodiment, at least one of A and B may be a carbamoyl derivative

represented by or . When one of A and B is the carbamoyl derivative, the other is not hydrogen.

Since the compound has two chiral carbons at the 1 ^st and 2 ^nd positions from the X substituted phenyl alkyl carbamate derivative group, they may be in the form of a racemate, an enantiomer, a diastereomer, a mixture of enantiomers, or a mixture of diastereomers.

In a concrete embodiment, the compound may be selected from the group consisting of:

1 -(2-chlorophenyl)-2-carbamoyloxypropyl- 1 -carbamate,

1 -(2-chlorophenyl)-2-carbamoyloxypropyl- 1 -N-methylcarbamate,

1 -(2-chlorophenyl)-2-carbamoyloxypropyl- 1 -N-propyl carbamate

1 -(2-chlorophenyl)-2-carbamoyloxybutyl- 1 -carbamate,

1 -(2-chlorophenyl)-2-carbamoyloxy-3 -methyl -butyl- 1 -carbamate,

1 -(2-chlorophenyl)-2-carbamoyloxyhexyl- 1 -carbamate, 1 -(2-iodophenyl)-Z-carbamoyloxypropyl- 1 -carbamate,

1 -(2-iodophenyl)-2-carbamoyloxybutyl- 1 -carbamate,

l-(2-iodophenyl)-2-carbamoyloxy-3 -methyl-butyl- 1 -carbamate,

1 -(2-iodophenyl)-2-carbamoyloxyhexyl- 1 -carbamate,

1 -(2-fluorophenyl)-2-carbamoyloxypropyl- 1 -carbamate,

1 -(2-fluorophenyl)-2-carbamoyloxybutyl-l -carbamate,

1 -(2-fluorophenyl)-2-carbamoyloxy-3 -methyl -butyl- 1 -carbamate,

1 -(2-fluorophenyl)-2-carbamoyloxyhexyl- 1 -carbamate,

1 -(2,4-dichlorophenyl)-2-carbamoyloxypropyl- 1 -carbamate,

1 -(2,4-dichlorophenyl)-2-carbamoyloxybutyl- 1 -carbamate,

l-(2,4-dichlorophenyl)-2-carbamoyloxy-3-methyl-butyl-l-ca rbamate,

1 -(2,4-dichlorophenyl)-2-carbamoyloxyhexyl- 1 -carbamate,

1 -(2,6-dichlorophenyl)-2-carbamoyloxypropyl- 1 -carbamate,

1 -(2,6-dichlorophenyl)-2-carbamoyloxybutyl- 1 -carbamate,

1 -(2,6-dichlorophenyl)-2-carbamoyloxy-3 -methyl-butyl- 1 -carbamate,

1 -(2,6-dichlorophenyl)-2-carbamoyloxyhexyl- 1 -carbamate,

1 -(2-chlorophenyl)- 1 -(methoxy)-ethyl-2-carbamate,

1 -(2-fluorophenyl)- 1 -(methoxy)-ethyl-2-carbamate,

1 -(2-iodophenyl)- 1 -(methoxy)-ethyl-2-carbamate,

1 -(2-iodophenyl)- 1 -(methoxy)-propyl-2-carbamate,

1 -(2-iodophenyl)- 1 -(methoxy)-propyl-2-N-methylcarbamate,

1 -(2-iodophenyl)- 1 -(methoxy)-propyl-2-N-propyl carbamate,

1 -(2-iodophenyl)- 1 -(methoxy)-propyl-2-N-isopropyl carbamate,

1 -(2-iodophenyl)- 1 -(methoxy)-propyl-2-N-cyclopropylcarbamate,

1 -(2-iodophenyl)- 1 -(methoxy)-propyl-2-N-cyclohexyl carbamate,

1 -(2-iodophenyl)- 1 -(methoxy)-propyl-2-N-benzyl carbamate,

1 -(2-iodophenyl)- 1 -(methoxy)-propyl-2-N-bicyclo[2,2, 1 Jheptanecarbamate

1 -(2-iodophenyl)- 1 -(methoxy)-butyl-2-carbamate,

1 -(2-iodophenyl)- 1 -(methoxy)-butyl-2-N-methyl carbamate,

1 -(2-iodophenyl)- 1 -(methoxy)-butyl-2-N-propylcarbamate,

1 -(2-iodophenyl)- 1 -(methoxy)-butyl-2-N-isopropylcarbamate,

1 -(2-iodophenyl)- 1 -(methoxy)-butyl-2-N-cyclopropyl carbamate, l-(2-iodophenyl)- l-(methoxy)-butyl-2-N-cyclohexylcarbamate, l-(2-iodophenyl)- l-(methoxy)-butyl-2-N-benzylcarbamate,

1 -(2-iodophenyl)- 1 -(methoxy)-butyl-2-N-bicyclo[2,2, 1 Jheptanecarbamate,

1 -(2-iodophenyl)- 1 -(methoxy)3 -methyl -butyl-2-carbamate,

l-(2-iodophenyl)- 1 -(methoxy)-3 -methyl-butyl-2-N-methyl carbamate,

l-(2-iodophenyl)- l-(methoxy)-3-methyl-butyl-2-N-propylcarbamate,

1 -(2-iodophenyl)- 1 -(methoxy)-3 -methyl-butyl -2-N-isopropyl carbamate,

1 -(2-iodophenyl)- 1 -(methoxy)-3 -methyl-butyl-2-N-cyclopropyl carbamate, l-(2-iodophenyl)- l-(methoxy)-3-methyl-butyl-2-N-cyclohexylcarbamate,

1 -(2-iodophenyl)- l-(methoxy)-3-methyl-butyl-2-N-benzylcarbamate,

1 -(2-iodophenyl)- 1 -(methoxy)-3 -methyl-butyl-2-N-bicyclo [2,2, 1 ]heptanecarbamate, l-(2-iodophenyl)- 1 -(methoxy)-hexyl-2-carbamate,

l-(2-iodophenyl)- l-(methoxy)-hexyl-2-N-methylcarbamate,

l-(2-iodophenyl)- l-(methoxy)-hexyl-2-N-propylcarbamate,

l-(2-iodophenyl)- l-(methoxy)-hexyl-2-N-isopropylcarbamate,

1 -(2-iodophenyl)- 1 -(methoxy)-hexyl-2-N-cyclopropyl carbamate,

1 -(2-iodophenyl) l-(methoxy)-hexyl-2-N-cyclohexylcarbamate,

1 -(2-iodophenyl) l-(methoxy)-hexyl-2-N-benzylcarbamate,

1 -(2-iodophenyl) 1 -(methoxy)-hexyl-2-N-bicyclo[2,2, 1 ]heptanecarbamate,

1 -(3-iodophenyl)- 1 -(methoxy)-propyl-2-carbamate,

l-(3-iodophenyl)- 1 -(methoxy)-butyl-2-carbamate,

l-(3-iodophenyl)- 1 -(methoxy)3 -methyl -butyl -2-carbamate,

l-(3-iodophenyl)- 1 -(methoxy)-hexyl-2-carbamate,

1 -(2-fluorophenyl )- 1 -(methoxy)-propyl-2-carbamate,

1 -(2-fluorophenyl )- 1 -(methoxy)-propyl-2-N-methylcarbamate,

1 -(2-fluorophenyl )- 1 -(methoxy)-propyl-2-N-propyl carbamate,

1 -(2-fluorophenyl )- 1 -(methoxy)-propyl-2-N-isopropylcarbamate,

1 -(2-fluorophenyl )- 1 -(methoxy)-propyl-2-N-cyclopropylcarbamate,

1 -(2-fluorophenyl )- 1 -(methoxy)-propyl -2 -N-cyclohexyl carbamate,

1 -(2-fluorophenyl )- 1 -(methoxy)-propyl-2-N-benzylcarbamate,

1 -(2-fluorophenyl )- 1 -(methoxy)-propyl-2-N-bicyclo[2,2, 1 Jheptanecarbamate 1 -(2-fluorophenyl )- 1 -(methoxy)-butyl-2-carbamate, 1 -(2-fluorophenyl)- 1 -(methoxy)-3 -methyl-butyl-2-carbamate,

1 -(2-fluorophenyl)- 1 -(methoxy)-hexyl-2-carbamate,

1 -(4-fluorophenyl)- 1 -(methoxy)-proyl-2-carbamate,

1 -(4-fluorophenyl)- 1 -(methoxy)-butyl-2-carbamate,

1 -(4-fluorophenyl)- 1 -(methoxy)-3 -methyl -butyl-2-carbamate,

1 -(4-fluorophenyl)- 1 -(methoxy)-hexyl-2-carbamate,

1 -(2-chlorophenyl)- 1 -(methoxy)-propyl-2-carbamate,

1 -(2-chlorophenyl)- 1 -(methoxy)-propyl-2-N-methyl carbamate,

1 -(2-chlorophenyl)- 1 -(methoxy)-propyl-2-N-propylcarbamate,

1 -(2-chlorophenyl)- 1 -(methoxy)-propyl-2-N-isopropylcarbamate,

1 -(2-chlorophenyl)- 1 -(methoxy)-propyl-2-N-cyclopropylcarbamate,

1 -(2-chlorophenyl)- 1 -(methoxy)-propyl-2-N-cyclohexyl carbamate,

1 -(2-chlorophenyl)- 1 -(methoxy)-propyl-2-N-benzylcarbamate,

1 -(2-chlorophenyl)- 1 -(methoxy)-propyl-2-N-bicyclo[2,2, 1 Jheptanecarbamate

1 -(2-chlorophenyl)- 1 -(methoxy)-butyl-2-carbamate,

1 -(2-chlorophenyl)- 1 -(methoxy)-3-methyl-butyl-2-carbamate,

1 -(2-chlorophenyl)- 1 -(methoxy)-hexyl-2-carbamate,

l-(2,3-dichlorophenyl)-l-(methoxy)-propyl-2-carbamate,

1 -(2,4-dichlorophenyl)- 1 -(methoxy)-propyl-2-carbamate,

1 -(2,4-dichlorophenyl)- 1 -(methoxy)-butyl-2-carbamate,

1 -(2,4-dichlorophenyl)- 1 -(methoxy)-3-methyl-butyl-2-carbamate,

1 -(2,4-dichlorophenyl)- 1 -(methoxy)-hexyl-2-carbamate,

1 -(2,6-dichlorophenyl)- 1 -(methoxy)-propyl-2-carbamate,

1 -(2,6-dichlorophenyl)- 1 -(methoxy)-butyl-2-carbamate,

1 -(2,6-dichlorophenyl)- 1 -(methoxy)-3-methyl-butyl-2-carbamate,

1 -(2,6-dichlorophenyl)- 1 -(methoxy)-hexyl-2-carbamate,

1 -(2-chlorophenyl)- 1 -(methoxymethoxy)-ethyl-2-carbamate,

1 -(2-fluorophenyl)- 1 -(methoxymethoxy)-ethyl-2-carbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-ethyl-2-carbamate,

1 -(2-chlorophenyl)- 1 -(methoxymethoxy)-propyl-2-carbamate,

1 -(2-chlorophenyl)- 1 -(methoxymethoxy)-propyl-2-N-methylcarbamate,

1 -(2-chlorophenyl)- 1 -(methoxymethoxy)-propyl-2-N-propyl carbamate, 1 -(2-chlorophenyl)- 1 -(methoxymethoxy)-propyl-2-N-isopropyl carbamate,

1 -(2-chlorophenyl)- 1 -(methoxymethoxy)-propyl-2-N-cyclopropyl carbamate,

1 -(2-chlorophenyl)- 1 -(methoxymethoxy)-propyl-2-N-cyclohexylcarbamate,

1 -(2-chlorophenyl)- 1 -(methoxymethoxy)-propyl-2-N-benzyl carbamate,

l-(2-chlorophenyl)-l-(methoxymethoxy)-propyl-2-N-bicyclo[ 2,2,l]heptanecarbamate

1 -(2-chlorophenyl)- 1 -(methoxymethoxy)-butyl-2-carbamate,

1 -(2-chlorophenyl)- 1 -(methoxymethoxy)-3 -methyl-butyl-2-carbamate,

1 -(2-chlorophenyl)- 1 -(methoxymethoxy)-hexyl-2-carbamate,

l-(2,3-dichlorophenyl)-l-(methoxymethoxy)-propyl-2-carbam ate,

1 -(2,4-dichlorophenyl)- 1 -(methoxymethoxy)-propyl-2-carbamate,

1 -(2,4-dichlorophenyl)- 1 -(methoxymethoxy)-butyl-2-carbamate,

1 -(2,4-dichlorophenyl)- 1 -(methoxymethoxy)-3 -methyl -butyl-2-carbamate,

1 -(2,4-dichlorophenyl)- 1 -(methoxymethoxy)-hexyl-2-carbamate,

1 -(2,5-dichlorophenyl)- 1 -(methoxymethoxy)-propyl-2-carbamate,

1 -(2,6-dichlorophenyl)- 1 -(methoxymethoxy)-propyl-2-carbamate,

1 -(2,6-dichlorophenyl)- 1 -(methoxymethoxy)-butyl-2-carbamate,

1 -(2,6-dichlorophenyl)- 1 -(methoxymethoxy)-3 -methyl -butyl-2-carbamate,

1 -(2,6-dichlorophenyl)- 1 -(methoxymethoxy)-hexyl-2-carbamate,

1 -(2-fluorophenyl)- 1 -(methoxymethoxy)-propyl-2-carbamate,

1 -(2-fluorophenyl)- 1 -(methoxymethoxy)-propyl-2-N-m ethyl carbamate,

1 -(2-fluorophenyl)- 1 -(methoxymethoxy)-propyl-2-N-propylcarbamate,

-(2-fluorophenyl)- 1 -(methoxymethoxy)-propyl-2-N-isopropyl carbamate,

-(2-fluorophenyl)- 1 -(methoxymethoxy)-propyl-2-N-cyclopropyl carbamate,

-(2-fluorophenyl)- 1 -(methoxymethoxy)-propyl-2-N-cyclohexyl carbamate,

-(2-fluorophenyl)- 1 -(methoxymethoxy)-propyl-2-N-benzyl carbamate,

-(2-fluorophenyl)- 1 -(methoxymethoxy)-propyl-2-N-bicyclo[2,2, 1 ]heptanecarbamate -(2-fluorophenyl)- 1 -(methoxymethoxy)-butyl-2-carbamate,

-(2-fluorophenyl)- 1 -(methoxymethoxy)-3 -methyl -butyl-2-carbamate,

-(2-fluorophenyl)- 1 -(methoxymethoxy)-hexyl-2-carbamate,

-(4-fluorophenyl)- 1 -(methoxymethoxy)-propyl-2-carbamate,

-(4-fluorophenyl)- 1 -(methoxymethoxy)-butyl-2-carbamate,

-(4-fluorophenyl)- 1 -(methoxymethoxy)-3 -methyl -butyl-2-carbamate, 1 -(4-fluorophenyl)- 1 -(methoxymethoxy)-hexyl-2-carbamate,

1 -(2,6-difluorophenyl)- 1 -(methoxymethoxy)-propyl-2-carbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-propyl-2-carbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-propyl-2-N-methyl carbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-propyl-2-N-propylcarbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-propyl-2-N-isopropyl carbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-propyl-2-N-cyclopropyl carbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-propyl-2-N-cyclohexylcarbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-propyl-2-N-benzylcarbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-propyl-2-N-bicyclo[2,2, 1 Jheptanecarbamate

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-butyl-2-carbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-butyl-2-N-methylcarbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-butyl-2-N-propylcarbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-butyl-2-N-isopropyl carbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-butyl-2-N-cyclopropylcarbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-butyl-2-N-cyclohexylcarbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-butyl-2-N-benzylcarbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-butyl-2-N-bicyclo[2,2, 1 ]heptanecarbamate

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-3 -methyl -butyl-2-carbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-3 -methyl -butyl-2-N-methylcarbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-3-methyl-butyl-2-N-propylcarbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-3-methyl-butyl-2-N-isopropyl carbamate, l-(2-iodophenyl)-l-(methoxymethoxy)-3-methyl-butyl-2-N-cyclo propylcarbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-3-methyl-butyl-2-N-cyclohexyl carbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-3-methyl-butyl-2-N-benzylcarbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-3 -methyl-butyl-2-N- bicyclo[2,2, 1 Jheptanecarbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-hexyl-2-carbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-hexyl-2-N-methylcarbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-hexyl-2-N-propylcarbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-hexyl-2-N-isopropyl carbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-hexyl-2-N-cyclopropyl carbamate, 1 -(2-iodophenyl)- 1 -(methoxymethoxy)-hexyl-2-N-cyclohexyl carbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-hexyl-2-N-benzylcarbamate,

1 -(2-iodophenyl)- 1 -(methoxymethoxy)-hexyl-2-N-bicyclo[2,2, 1 ]heptanecarbamate

1 -(3 -iodophenyl)- 1 -(methoxymethoxy)-propyl-2-carbamate,

1 -(3 -iodophenyl)- 1 -(methoxymethoxy)-butyl-2-carbamate,

l-(3-iodophenyl)-l-(methoxymethoxy)-3-methyl-butyl-2-carbama te,

1 -(3 -iodophenyl)- 1 -(methoxymethoxy)-hexyl-2-carbamate,

1 -(2-chlorophenyl)-2-(methoxymethoxy)-propyl- 1 -carbamate,

1 -(2-chlorophenyl)-2-(methoxy)-propyl- 1 -carbamate, and

a racemate of the compound, an enantiomer of the compound, a diastereomer of the compound, a mixture of enantiomers of the compound, or a mixture of diastereomers of the compound.

Alternatively, the compound may be in the form of a pharmaceutically acceptable salt.

The pharmaceutically acceptable salt may include an additional salt of acid or base, and its stereochemical isomer. For example, the compound may be in the form of an additional salt of an organic or inorganic acid. The salt may not be specially limited, and include any salts that maintain the activities of their parent compounds, with no undesirable effects, in the subject, when they are administered to the subject. Such salts may include inorganic and organic salts, such as salts of acetic acid, nitric acid, aspartic acid, sulfonic acid, sulfuric acid, maleic acid, glutamic acid, formic acid, succinic acid, phosphoric acid, phthalic acid, tannic acid, tartaric acid, hydrobromic acid, propionic acid, benzene sulfonic acid, benzoic acid, stearic acid, lactic acid, bicarbonic acid, bisulfuric acid, bitartaric acid, oxalic acid, butyric acid, calcium edetate, carbonic acid, chlorobezoic acid, citric acid, edetic acid, toluenesulfonic acid, fumaric acid, gluceptic acid, esilic acid, pamoic acid, gluconic acid, methyl nitric acid, malonic acid, hydrochloric acid, hydroiodic, hydroxynaphtholic acid, isethionic acid, lactobionic acid, mandelic acid, mucic acid, naphthylic acid, muconic acid, p-nitromethanesulfonic acid, hexamic acid, pantothenic acid, monohydrogen phosphoric acid, dihydrogen phosphoric acid, salicylic acid, sulfamic acid, sulfanilic acid, methane sulfonic acid, and the like. The additional salts of base may include salts of akali metal or alkaline earth metal, such as salts of ammonium, lithium, sodium, potassium, magnesium, calcium, and the like; salts having an organic base, such as benzathine, N-methyl-D- glucamine, hydrabamine, and the like; and salts having an amino acid such as arginine, lysine, and the like. In addition, these salts may be converted to a released form by treating with a proper base or acid.

Another embodiment provides a pharmaceutical composition containing a phenyl alkyl carbamate derivative compound represented by Chemical Formula 1 ; a racemate, an enantiomer, a diastereomer, a mixture of enantiomers, or a mixture of diastereomers thereof; or a pharmaceutically acceptable salt thereof, as an active ingredient.

As demonstrated in the following experimental examples, the compound of Chemical Formula 1 ; a racemate, an enantiomer, a diastereomer, a mixture of enantiomers, or a mixture of diastereomers thereof; or pharmaceutically acceptable salt thereof exhibits an excellent effect on muscle relaxation. Thus, the pharmaceutical composition may be a pharmaceutical composition for muscle relaxation (muscle relaxant).

Therefore, another embodiment provides a pharmaceutical composition for muscle relaxation containing a compound of Chemical Formula 1; a racemate, an enantiomer, a diastereomer, a mixture of enantiomers, or a mixture of diastereomers thereof; or a pharmaceutically acceptable salt thereof, as an active ingredient.

In addition, since a muscle relaxant can be used for improving (alleviating) and/or treating symptoms of diseases associated with muscle spasm, the pharmaceutical composition capable of acting as muscle relaxant may also be used as a pharmaceutical composition for preventing and/or treating a muscle spasm associated disease, for example, vascular disorders of the spinal cord, spastic spinal paralysis, cervical spondylosis, cerebral palsy, sequelae of injuries (spinal cord injuries, head injuries), spinocerebellar degeneration, and the like. Therefore, another embodiment provides a pharmaceutical composition for preventing and/or treating a muscle spasm associated disease containing a compound of Chemical Formula 1 ; a racemate, an enantiomer, a diastereomer, a mixture of enantiomers, or a mixture of diastereomers thereof; or a pharmaceutically acceptable salt thereof, as an active ingredient.

A muscle spasm associated disease is a sudden, involuntary contraction of a muscle. It is generally known to the relevant art that muscle spasm associated diseases are not associated with abnormal or excessive neuronal activity in the brain, such as seizure. Therefore, in the present invention, the muscle spasm associated disease is not a disease associated with abnormal or excessive neuronal activity in the brain, such as seizure.

The pharmaceutical composition may be formulated in various forms for oral or parenteral administration. For example, the pharmaceutical composition may be formulated in the oral administration form, such as a tablet, pill, soft or hard capsule, liquid, suspension, emulsion, syrup, granules, elixirs, and the like. In addition to the active ingredient, the oral administration form may further include pharmaceutically acceptable and conventional components, for example, a diluent such as lactose, dextrose, sucrose, mannitol, sorbitol, cellulose, glycine, and the like; a lubricant such as silica, talc, stearic acid, magnesium or calcium salt thereof, polyethyleneglycol, and the like.

In the case that the oral administration form is a tablet, it may further include a binder such as magnesium aluminium silicate, starch paste, gelatin, tragacanth, methylcellulose, sodium carboxymethylcellulose, polyvinylpirrolidine, and the like; and optionally include one or more additives selected from the group consisting of a disintegrant such as starch, agar, arginic acid or sodium salt thereof, an absorbent, a colorant, a flavoring, a sweetener, and the like.

Alternatively, the pharmaceutical composition may also be formulated in a parenteral administration form, which can be administered by subcutaneous injection, intravenous injection, intramuscular injection, injection into thoracic cavity, and the like. In order to formulate the parenteral administration form, the pharmaceutical composition may be prepared as a solution or suspension wherein the active ingredient is dissolved in water together with a stabilizer and/or a buffering agent, and such solution or suspension formulation may be prepared as a dosage form in ample or vial.

The pharmaceutical composition may be sterilized, and/or include further additives such as a preservative, a stabilizer, a hydrating agent, an emulsification accelerator, a salt and/or buffering agent for osmoregulation, and the like, and/or further therapeutically effective ingredients. The pharmaceutical composition may be formulated by any conventional method for mixing, granulating, coating, and the like.

The pharmaceutical composition may be administered to a mammal including human, in the therapeutically effective amount of 0.01 to 750 mg/kg(body weight), preferably 0.1 to 500 mg/kg(body weight) per one day, based on the active ingredient. The term "therapeutically effective amount" may refer to an amount of the active gradient capable of exhibiting the effect of alleviating and/or treating pain. The therapeutically effective amount may be administered through oral or parenteral pathway, one or two or more times per one day.

The therapeutically effective amount and the administration pathway of the present pharmaceutical composition may be properly adjusted by a person skilled in the relevant field considering the conditions of the subject (patient), desired effects, and the like. Another embodiment provides a method of muscle relaxation comprising administering a therapeutically effective amount of a phenyl alkyl carbamate derivative compound represented by Chemical Formula 1 ; a racemate, an enantiomer, a diastereomer, a mixture of enantiomers, or a mixture of diastereomers thereof; or a pharmaceutically acceptable salt thereof, to a subject in need of muscle relaxation. The method of muscle relaxation may further include the step of identifying the subject in need of muscle relaxation, prior to the step of administration.

Another embodiment provides a method of treating and/or preventing a muscle spasm associated disease, comprising administering a therapeutically effective amount of a phenyl alkyl carbamate derivative compound represented by Chemical Formula 1 ; a racemate, an enantiomer, a diastereomer, a mixture of enantiomers, or a mixture of diastereomers thereof; or a pharmaceutically acceptable salt thereof, to a subject in need of treating and/or preventing a muscle spasm associated disease. The method of treating and/or preventing a muscle spasm associated disease may further include the step of identifying the subject in need of treating and/or preventing a muscle spasm associated disease, prior to the step of administration.

The administration may be conducted by oral or parenteral administration such as subcutaneous injection, intravenous injection, intramuscular injection, injection into thoracic cavity, and the like.

The subject may be a mammal including human or cells and/or tissues separated therefrom.

Another embodiment provides a phenyl alkyl carbamate derivative compound represented by Chemical Formula 1; a racemate, an enantiomer, a diastereomer, a mixture of enantiomers, or a mixture of diastereomers thereof; or a pharmaceutically acceptable salt thereof, a for use in muscle relaxation.

Another embodiment provides a phenyl alkyl carbamate derivative compound represented by Chemical Formula 1; a racemate, an enantiomer, a diastereomer, a mixture of enantiomers, or a mixture of diastereomers thereof; or a pharmaceutically acceptable salt thereof, for use in treating and/or preventing a muscle spasm associated disease.

Another embodiment provides a use of phenyl alkyl carbamate derivative compound represented by Chemical Formula 1; a racemate, an enantiomer, a diastereomer, a mixture of enantiomers, or a mixture of diastereomers thereof; or a pharmaceutically acceptable salt thereof, in muscle relaxation or in preparing a muscle relaxant.

Another embodiment provides a use of a phenyl alkyl carbamate derivative compound represented by Chemical Formula 1 ; a racemate, an enantiomer, a diastereomer, a mixture of enantiomers, or a mixture of diastereomers thereof; or a pharmaceutically acceptable salt thereof, in treating and/or preventing a muscle spasm associated disease or in preparing a pharmaceutical composition for treating and/or preventing a muscle spasm associated disease.

The carbamate compound of the present invention may prepared by the following reaction formula.

Reaction Formula I: Synthesis of Diol-1

trans olefin Diol

A diol compound used in the synthesis of the carbamate compound may be synthesized by dihydroxylation of a trans-olefin compound. A diol compound having optical activity may be synthesized using a sharpless asymmetric dihydroxylation catalyst.

Reaction Formula II : Synthesis of Diol-2

p

Protected alcohol

As indicated in the Reaction Formula II, the optically active substance of diol may also be synthesized using a reduction reagent after synthesizing a hydroxy-ketone compound using Haloro-Mandelic acid. In the Reaction Formula II, PG may be Trialkyl Silyl group(TMS, TES, TIPS, TBDMS, TBDPS), Ether group[MOM(Mothoxymethyl ether), MEM(2- Methoxyethoxymethyl ether), BOM(Benzyloxymethyl ether). MTM(Methylthiomethyl ether), SEM(2-(Trimethylsilyl)ethoxymethyl ether), PMBM(p-Methoxybenzyl ether), THP(Tetrahydropyranyl ether), Allyl ether, Trityl ether, Ester group[Ac(acetate), Bz(Benzoate), Pv(Pivaloate), Cbz(Benzyl carbonate), BOC(t-Butyl carbonate), Fmoc(9- Fulorenylmethyl)carbaonate, Alloc(Allyl Carbonate), Troc(Trichloroehtyl carbonate), or p- Methoxybenzoate, Methyl carbonate, and so on. Reaction Formula HI : Carbamation reaction- 1

As a highly selectivity form of regioisomer of single carbamate of diol having halogen substituent at phenyl ring.

Reaction Formula IV : Carbamation reaction-2

Two substances in the form of regioisomers of a single carbamate of diol having halogen substituent at phenyl ring may be separated by flash column chromatography to obtain two kinds of single carbamate compounds.

A and B is alkyl or alkoxy alky ether such as methoxy methyl ether(MOM) or a carbamoyl derivative represented by , and R2 may be selected from the group consisting of hydrogen, a linear or branched alkyl group of C1-C4, for example C1-C3, a cycloalkyl group of C3-C8, for example C3-C7, and benzyl group, and more specifically, R2 may be selected from the group consisting of hydrogen, methyl group, propyl group, isopropyl group, cyclopropyl group, cyclohexyl group, bicycloheptane group, and benzyl group.

EXAMPLE

The present invention is further explained in more detail with reference to the following examples. These examples, however, should not be interpreted as limiting the scope of the present invention in any manner.

Preparation Example 1: Synthesis of l-(2-chlorophenyl)-trans-l-propene

48ml of 2-chlorobenzenaldehyde (0.42mol) and 49.7ml of 3-pentanone (0.47mol) were dissolved in 600mL of hexane in flask, and then stirred with raising the temperature. 53.6ml of Boron trifluoride etherate (BF ₃ OEt ₂ , 0.42mol) was added to the resultant under reflux conditions. When the reaction was completed, water was added thereto. After layer separation, the obtained organic layer was washed twice with IM sodium hydroxide solution (IM NaOH), and then the separated organic layer was washed with water. The separated organic layer was dehydrated with anhydrous magnesium sulfate (MgSC ) and concentrated. The concentrated residue was purified by a silica gel column chromatography to produce the title compound (38g, yield 58%). 1H NMR(400MHz, CDC1 ₃ ) 61.94(d, J=4.8Hz, 3H), 6.24(m, 1H), 6.78(d, J=14Hz, 1H), 7.11~7.51(m, 4H)

Preparation Example 2: Synthesis of l-(2-chlorophenyl)-trans-l-butene The substantially same method as described in Preparation Example 1 was conducted, except that 3-heptanone was used instead of 3-pentanone, to obtain the title compound (2.9g, yield 83%).

1H NMR(400MHz, CDC1 ₃ ) 51.14(d, J=7.6Hz, 3H), 2.29~2.33(m, 2H), 6.28(dt, J=16Hz, 6.4Hz, 1H), 6.78(d, J=15.6Hz, 1H), 7.13~7.54(m, 4H)

Preparation Example 3: Synthesis of l-(2-chIorophenyl)-3-methyl-trans-l-butene

The substantially same method as described in Preparation Example 1 was conducted, except that 2,6-dimethyl-heptan-4-one was used instead of 3-pentanone, to obtain the title compound (8.0g, yield 50-90%).

Ή NMR(400MHz, CDC1 ₃ ) 61.14(d, J=6.8Hz, 6H), 2.25~2.57(m, 1H), 6.20(dd, J=16Hz, 7.2Hz, 1H), 7.64(d, J=16Hz, 1H), 7.12~7.54(m, 4H)

Preparation Example 4: Synthesis of l-(2-chlorophenyl)-trans-l-hexene

The substantially same method as described in Preparation Example 1 was conducted, except that 6-undecanone was used instead of 3-pentanone, to obtain the title compound (lOg, yield 85%).

Ή NMR(400MHz, CDC1 ₃ ) 50.96(t, J=7.2Hz, 3H), 1.33~1.56(m, 4H), 2.26~2.32(m, 4H), 6.24(dt, J=15.6Hz, 7Hz, 1H), 6.78(d, J=16Hz, 1H), 7.13~7.54(m, 4H)

Preparation Example 5: Synthesis of l-(2,4-dichlorophenyl)-trans-l-propene

The substantially same method as described in Preparation Example 1 was conducted, except that 2,4-dichlorobenzenaldehyde was used instead of 2-chlorobenzenaldehyde, to obtain the title compound (2.4g, yield 57%).

1H NMR(400MHz, CDC1 ₃ ) 51.95(dd, J=6.8Hz, 1.6Hz, 3H), 6.24(m, 1H),

J=15.6Hz, 1H), 7.18~7.44(m, 3H)

Preparation Example 6: Synthesis of l-(2,4-dichlorophenyl)-trans-l-butene

The substantially same method as described in Preparation Example 5 was conducted, except that 3-heptanone was used instead of 3-pentanone, to obtain the title compound (2.1g, yield 90%).

1H NMR(400MHz, CDC1 ₃ ) 61.14(d, J=7.6Hz, 3H), 2.20~2.33(m, 2H), 6.26(dt, J=16Hz, 6.8Hz, 1H), 6.70(d, J=15.6Hz, 1H), 7.18~7.46(m, 3H)

Preparation Example 7: Synthesis of l-(2,6-dichlorophenyl)-3-methyl-trans-l- butene

The substantially same method as described in Preparation Example 5 was conducted, except that 2,6-dimethyl-heptan-4-one was used instead of 3-pentanone, to obtain the title compound (0.23g, yield 10-40%).

1H NMR(400MHz, CDC1 ₃ ) 61.15(d, J=6.8Hz, 6H), 2.53~2.58(m, 1H), 6.19(dd, J=16.4Hz, 6.8Hz, 1H), 6.31(d, J=16.4Hz, 1H), 7.18~7.46(m, 3H)

Preparation Example 8: Synthesis of l-(2,4-dichlorophenyl)-trans-l-hexene

The substantially same method as described in Preparation Example 5 was conducted, except that 6-undecanone was used instead of 3-pentanone, to obtain the title compound (3.2g, yield 40-80%). 1H NMR(400MHz, CDC1 ₃ ) 50.96(t, J=7.2Hz, 3H), 1.38~1.52(m, 4H), 2.25~2.31(m, 2H), 6.22(dt, J=l 5.6Hz, 6.8Hz, 1H), 6.70(d, J=15.6Hz, 1H), 7.18~7.46(m, 3H)

Preparation Example 9: Synthesis of l-(2,6-dichlorophenyl)-trans-l-propene

The substantially same method as described in Preparation Example 1 was conducted, except that 2,6-dichlorobenzenaldehyde was used instead of 2-chlorobenzenaldehyde, to obtain the title compound (0.4g, yield 10-40%).

1H NMR(400MHz, CDC1 ₃ ) 51.98(d, J=8Hz, 3H), 6.23-6.3 l(m, 1H), 6.40(d, J=16Hz, 1H), 7.05~7.32(m, 3H)

Preparation Example 10: Synthesis of l-(2,6-dichlorophenyl)-trans-l-butene

The substantially same method as described in Preparation Example 9 was conducted, except that 3-heptanone was used instead of 3-pentanone, to obtain the title compound (1.2g, yield 10-40%).

Ή NMR(400MHz, CDC1 ₃ ) 51.17(t, J=7.6Hz, 3H), 2.30~2.37(m, 2H), 6.29(dt, J=16.4Hz, 6Hz, 1H), 6.37(d, J=16.4Hz, 1H), 7.05~7.32(m, 3H)

Preparation Example 11: Synthesis of l-(2,6-dichlorophenyl)-3-methyl-trans-l- butene

The substantially same method as described in Preparation Example 9 was conducted, except that 2,6-dimethyl-heptan-4-one was used instead of 3-pentanone, to obtain the title compound (0.23g, yield 10-40%).

1H NMR(400MHz, CDC1 ₃ ) 61.15(d, J=6.8Hz, 6H), 2.53~2.58(m, 1H), 6.19(dd, J=16.4Hz, 6.8Hz, 1H), 6.3 l(d, J=16.4Hz, 1H), 7.05~7.32(m, 3H)

Preparation Example 12: Synthesis of l-(2,6-dichlorophenyl)-trans-l-hexene

The substantially same method as described in Preparation Example 9 was conducted, except that 6-undecanone was used instead of 3-pentanone, to obtain the title compound (0.2g, yield 10-40%).

1H NMR(400MHz, CDC1 ₃ ) 50.99(t, J=7.2Hz, 3H),1.14~1.59(m, 4H), 2.30~2.36(m, 2H), 6.24(dt, J=16Hz, 6.6Hz, 1H), 6.38(d, J=16.4Hz, 1H), 7.05~7.33(m, 3H)

Preparation Example 13: Synthesis of l-(2,3-dichlorophenyl)-trans-l-propene

The substantially same method as described in Preparation Example 1 was conducted, except that 2,3-dichlorobenzenaldehyde was used instead of 2-chlorobenzenaldehyde, to obtain the title compound (0.2g, yield 10-40%).

1H NMR(400MHz, CDC1 ₃ ) 61.94(d, J=4.8Hz, 3H), 6.24(m, 1H), 6.78(d, J=14Hz, 1H), 7.11-7.5 l(m, 3H)

Preparation Example 14: Synthesis of l-(2-chlorophenyl)-(S,S)-l,2-propanediol

l-(2-chlorophenyl)-trans-l-propene(1.5g, Preparation Example 1) was dissolved in 30mL of the mixture of t-BuOH/H ₂ 0 (1 :1(V/V)). At 0 ^° C , AD-mix-a (Aldrich, U.S.A.) (13.7g) and methane sulfone amide (CH ₃ S0 ₂ NH ₂ , 0.76g, 0.0080mol) were added thereto and stirred for overnight. When the reaction was completed, the obtained product was washed with an aqueous solution of sodium sulfite (Na ₂ S0 ₃ ) and ethylacetate (EA). Then, the organic layer was dehydrated with anhydrous magnesium sulfate (MgS0 ₄ ), filtrated, and concented under reduced pressure. The concentrated residue was purified by a silica gel column chromatography to produce the title compound (1.65g, yield 90%).

1H NMR(400MHz, CDC1 ₃ ) 61.20(d, J=6.4Hz, 3H), 2.48(d, J=4.0Hz 1H), 2.92(d, J=4.4Hz, 1H), 3.93~3.97(m, 1H), 4.97(t, J=4.8Hz, 1H), 7.22~7.51(m, 4H)

¹³ CNMR(100MHz,CDCl ₃ ) 618.8, 71.5, 74.4, 127.1, 128.1, 128.9, 129.5, 132.6, 138.9

Preparation Example 15: Synthesis of l-(2-chlorophenyl)-(R,R)-l,2-propanedioI

l-(2-chlorophenyl)-trans-l-propene (2.5g, Preparation Example 1) was dissolved in 50mL of the mixture of t-BuOH/H ₂ 0 (1 :1 (V/V)). At 0 ^° C , AD-mix-a (Aldrich, U.S.A.) (23.5g) and methane sulfone amide (CH ₃ S0 ₂ NH ₂ , 1.27g, 0.013mol) were added thereto and stirred for overnight. When the reaction was completed, the obtained product was washed with an aqueous solution of sodium sulfite (Na ₂ S0 ₃ ) and ethylacetate (EA). Then, the organic layer was dehydrated with anhydrous magnesium sulfate (MgS0 ₄ ), filtrated, and concented under reduced pressure. The concentrated residue was purified by a silica gel column chromatography to produce the title compound (2.96g, yield 90%).

1H NMR(400MHz, CDC1 ₃ ) 61.20(d, J=6.4Hz, 3H), 2.48(d, J=4.0Hz, 1H), 2.92(d, J=4.4Hz, 1H), 3.93~3.97(m, 1H), 4.97(t, J=4.8Hz, 1H), 7.22~7.51(m, 4H)

Preparation Example 16: Synthesis of the mixture of l-(2-chIorophenyl)-(S,S)-l,2- propan (R,R)-l,2-propanediol

l-(2-chlorophenyl)-trans-l-propene(6.53g, Preparation Example 1) was dissolved in

45mL of the mixture of acetone/t-BuOH/H ₂ 0(5:l :l V/V). At the room temperature, N- methylmorpholine-N-oxide (7.5 lg) and Os0 ₄ (0.54g) were added thereto and stirred for 2-3 hours. When the reaction was completed, the obtained product was washed with water and methylenechloride (MC). Then, the organic layer was dehydrated with anhydrous magnesium sulfate (MgS0 ₄ ), filtrated, and concented under reduced pressure. The concentrated residue was purified by a silica gel column chromatography to produce the title compound (6.42g, yield 80%).

1H NMR(400MHz, CDC1 ₃ ) 51.20(d, J=6.4Hz, 3H), 2.48(d, J=4.0Hz, 1H), 2.92(d, J=4.4Hz, 1H), 3.93~3.97(m, 1H), 4.97(t, J=4.8Hz, 1H), 7.22~7.51(m, 4H)

Preparation Example 17: Synthesis of l-(2-chlorophenyl)-(S,S)-l,2-butanediol

The substantially same method as described in Preparation Example 14 was conducted, except that l-(2-chlorophenyl)-trans-l-butene(Preparation Example 2) was used instead of l-(2- chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.36g, yield 95%).

Ή NMR(400MHz, CDC1 ₃ ) 61.01(t, J=7.4Hz, 3H), 1.52~1.65(m, 2H), 2.01(d, J=4.4Hz, 1H), 2.74(d, J=5.2Hz, 1H), 3.69~3.75(m, 1H), 5.05(t, J=5.0Hz, 1H), 7.23~7.54(m, 4H)

Preparation Example 18: Synthesis of l-(2-chlorophenyl)-(R,R)-l,2-butanediol

The substantially same method as described in Preparation Example 15 was conducted, except that l-(2-chlorophenyl)-trans-l-butene(Preparation Example 2) was used instead of l-(2- chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.84g, yield 60-95%).

1H NMR(400MHz, CDC1 ₃ ) 51.01(t, J=7.4Hz, 3H), 1.52~1.65(m, 2H), 2.01(d, J=4.4Hz, 1H), 2.74(d, J=5.2Hz, 1H), 3.69~3.75(m, 1H), 5.05(t, J=5.0Hz, 1H), 7.23~7.54(m, 4H)

Preparation Example 19: Synthesis of the mixture of l-(2-chlorophenyl)-(S,S)-l,2- butanediol and l-(2-chlorophenyl)-(R,R)-l,2-butanediol

The substantially same method as described in Preparation Example 16 was conducted, except that l-(2-chlorophenyl)-trans-l-butene(Preparation Example 2) was used instead of l-(2- chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (5.1g, yield 60-90%).

lH NMR(400MHz, CDC1 ₃ ) 51.01(t, J=7.4Hz, 3H), 1.52~1.65(m, 2H), 2.01 (d, J=4.4Hz, 1H), 2.74(d, J=5.2Hz, 1H), 3.69~3.75(m, 1H), 5.05(t, J=5.0Hz, 1H), 7.23~7.54(m, 4H)

Preparation Example 20: Synthesis of l-(2-chlorophenyl)-3-methyl-(S,S)-l,2- butanediol

The substantially same method as described in Preparation Example 14 was conducted, except that l-(2-chlorophenyl)-3-methyl-trans-l-butene(Preparation Example 3) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.96g, yield 60-90%).

1H NMR(400MHz, CDC1 ₃ ) 51.07(t, J=7.2Hz, 6H), 1.83~1.89(m, 1H), 1.92(d, J=5.6Hz, 1H), 2.69(d, J=6.4Hz, 1H), 3.53~3.56(m, 1H), 5.22~5.25(m, 1H), 7.23~7.55(m, 4H)

Preparation Example 21: Synthesis of l-(2-chlorophenyl)-3-methyl-(R,R)-l,2- butanediol

The substantially same method as described in Preparation Example 15 was conducted, except that l-(2-chlorophenyl)-3 -methyl-trans- l-butene(Preparation Example 3) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (4.2g, yield 60-90%).

1H NMR(400MHz, CDC1 ₃ ) 61.07(t, J=7.2Hz, 6H), 1.82~1.90(m, 1H), 1.93(d, J=5.6Hz, 1H), 2.79(d, J=6Hz, 1H), 3.53~3.57(m, 1H), 5.23~5.25(m, 1H), 7.23~7.54(m, 4H)

Preparation Example 22: Synthesis of the mixture of l-(2-chlorophenyl)-3-methyl- (S,S)-l,2-butanediol and l-(2-chIorophenyl)-3-methyl-(R,R)-l,2-butanediol

The substantially same method as described in Preparation Example 16 was conducted, except that l-(2-chlorophenyl)-3-methyl-trans-l-butene(Preparation Example 3) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.8g, yield 60-90%).

1H NMR(400MHz, CDC1 ₃ ) 61.07(t, J=7.2Hz, 6H), 1.83~1.90(m, 1H), 1.92(d, J=5.6Hz, 1H), 2.69(d, J=6.4Hz, 1H), 3.53~3.56(m, lH), 5.22~5.25(m, 1H), 7.23~7.55(m, 4H)

Preparation Example 23: Synthesis of l-(2-chlorophenyl)-(S,S)-l,2-hexanediol

The substantially same method as described in Preparation Example 14 was conducted, except that l-(2-chlorophenyl)-trans-l-hexene(Preparation Example 4) was used instead of l-(2- chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.37g, yield 90%).

Ή NMR(400MHz, CDC1 ₃ ) 60.90(t, J=7.2Hz, 3H), 1.35~1.65(m, 6H), 2.08(d, J=4.4Hz, 1H), 2.71(d, J=5.2Hz, 1H), 3.78~3.83(m, 1H), 5.04(t, J=5.0Hz, 1H), 7.23~7.53(m, 4H)

Preparation Example 24: Synthesis of l-(2-chlorophenyl)-(R,R)-l,2-hexanediol

The substantially same method as described in Preparation Example 15 was conducted, except that l-(2-chlorophenyl)-trans-l-hexene(Preparation Example 4) was used instead of l-(2- chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (4.2g, yield 60-90%).

1H NMR(400MHz, CDC1 ₃ ) δ0.91(ί, J=6.6Hz, 3H), 1.35~1.65(m, 6H), 2.08(d, J=4.8Hz, IH), 2.70(d, J=5.2Hz, IH), 3.80~3.83(m, IH), 5.05(t, J=5.0Hz, IH), 7.24~7.56(m, 4H)

Preparation Example 25: Synthesis of the mixture of l-(2-chiorophenyl)-(S,S)-l,2- hexanediol and l-(2-chlorophenyl)-(R,R)-l,2-hexanediol

The substantially same method as described in Preparation Example 16 was conducted, except that l-(2-chlorophenyl)-trans-l-hexene(Preparation Example 4) was used instead of l-(2- chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (7.9g, yield 60-90%).

1H NMPv(400MHz, CDC1 ₃ ) 50.90(t, J=7.2Hz, 3H), 1.26~1.55(m, 6H), 2.08(d, J=4.4Hz, IH), 2.71(d, J=5.6Hz, IH), 3.78~3.84(m, IH), 5.04(t, J=3.2Hz, IH), 7.24~7.55(m, 4H)

Preparation Example 26: Synthesis of l-(2,4-dichIorophenyI)-(S,S)-l,2-propanediol

The substantially same method as described in Preparation Example 14 was conducted, except that l-(2,4-ichlorophenyl)-trans-l-propene(Preparation Example 5) was used instead of 1 - (2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.33g, yield 60-95%).

Ή NMPv(400MHz, CDC1 ₃ ) 81.22(d, J=6.4Hz, 3H), 2.10(d, J=4.4Hz, IH), 2.71 (d, J=4.8Hz, IH), 3.90~3.95(m, IH), 4.94(t, J=5.0Hz, IH), 7.31 (dd, J=2.0Hz, J=8.0Hz, IH), 7.40(d, J=2.0Hz, IH), 7.49(d, J=8.4Hz, IH)

Preparation Example 27: Synthesis of l-(2,4-dichlorophenyl)-(R,R)-l,2-propanediol The substantially same method as described in Preparation Example 15 was conducted, except that l-(2,4-ichlorophenyl)-trans-l-propene(Preparation Example 5) was used instead of 1- (2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.45g, yield 60-95%).

1H NMR(400MHz, CDC1 ₃ ) 61.22(d, J=6.4Hz, 3H), 2.10(d, J=4.4Hz, 1H), 2.71 (d, J=4.8Hz, 1H), 3.90~3.95(m, 1H), 4.94(t, J=5.0Hz, 1H), 7.31~7.49(m, 3H)

Preparation Example 28: Synthesis of the mixture of l-(2,4-dichlorophenyl)-(S,S)- 1,2-propanediol and l-(2,4-dichIorophenyl)-(R,R)-l,2-propanediol

The substantially same method as described in Preparation Example 16 was conducted, except that l-(2,4-ichlorophenyl)-trans-l-propene(Preparation Example 5) was used instead of 1- (2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.45g, yield 60-95%).

1H NMR(400MHz, CDC1 ₃ ) 61.22(d, J=6.4Hz, 3H), 2.10(d, J=4.4Hz, 1H), 2.71 (d, J=4.8Hz, 1H), 3.90~3.95(m, 1H), 4.94(t, J=5.0Hz, 1H), 7.31~7.49(m, 3H)

Preparation Example 29: Synthesis of l-(2,4-dichlorophenyl)-(S,S)-l,2-butanediol

The substantially same method as described in Preparation Example 14 was conducted, except that l-(2,4-dichlorophenyl)-trans-l-butene(Preparation Example 6) was used instead of 1- (2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.32g, yield 90%).

1H NMPv(400MHz, CDC1 ₃ ) 51.02(t, J=7.4Hz, 3H), 1.54~1.61(m, 2H), 2.07(d, J=4.8Hz, 1H), 2.74(d, J=4.8Hz, 1H), 3.65~3.68(m, 1H), 5.01(t, J=5.0Hz, 1H), 7.31~7.49(m, 3H)

Preparation Example 30: Synthesis of l-(2,4-dichlorophenyl)-(R,R)-l,2-butanediol

The substantially same method as described in Preparation Example 15 was conducted, except that l-(2,4-dichlorophenyl)-trans-l-butene(Preparation Example 6) was used instead of 1- (2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.43g, yield 60-90%).

1H NMR(400MHz, CDC1 ₃ ) 51.02(t, J=7.4Hz, 3H), 1.54~1.61(m, 2H), 2.07(d, J=4.8Hz, 1H), 2.74(d, J=4.8Hz, 1H), 3.65~3.68(m, 1H), 5.01(t, J=5.0Hz, 1H), 7.31~7.49(m, 3H)

Preparation Example 31: Synthesis of the mixture of l-(2,4-dichlorophenyl)-(S,S)- 1,2-butanediol and l-(2,4-dichlorophenyI)-(R,R)-l,2-butanediol

The substantially same method as described in Preparation Example 16 was conducted, except that l-(2,4-dichlorophenyl)-trans-l-butene(Preparation Example 6) was used instead of 1- (2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.33g, yield 60-90%).

1H NMR(400MHz, CDC1 ₃ ) 61.02(t, J=7.4Hz, 3H), 1.54~1.61(m, 2H), 2.07(d, J=4.8Hz, 1H), 2.74(d, J=4.8Hz, 1H), 3.65~3.68(m, 1H), 5.01(t, J=5.0Hz, 1H), 77.31~7.49(m, 3H)

Preparation Example 32: Synthesis of l-(2,4-dichlorophenyl)-3-methyl-(S,S)-l,2- butanediol

The substantially same method as described in Preparation Example 14 was conducted, except that l-(2,4-dichlorophenyl)-3 -methyl-trans- l-butene(Preparation Example 7) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.25g, yield 60-95%). 1H NMR(400MHz, CDC1 ₃ ) 61.00(d, J=6.8Hz, 6H), 1.60~1.65(m, 1H), 2.35(d, J=4.0Hz, 1H), 3.12(d, J=8.4Hz, 1H), 4.13~4.18(m, 1H), 5.36(t, J=7.6Hz, 1H), 7.17~7.35(m, 3H)

Preparation Example 33: Synthesis of l-(2,4-dichIorophenyl)-3-methyl-(R,R)-l,2- butanediol

The substantially same method as described in Preparation Example 15 was conducted, except that l-(2,4-dichlorophenyl)-3 -methyl-trans- l-butene(Preparation Example 7) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.36g, yield 60-95%).

1H NMR(400MHz, CDC1 ₃ ) 61.00(d, J=6.8Hz, 6H), 1.60~1.65(m, 1H), 2.35(d, J=4.0Hz, 1H), 3.12(d, J=8.4Hz, 1H), 4.13~4.18(m, 1H), 5.36(t, J=7.6Hz, 1H), 7.17~7.35(m, 3H)

Preparation Example 34: Synthesis of the mixture of l-(2,4-dichlorophenyl)-3- methyl- -l,2-butanediol and l-(2,4-dichlorophenyl)-3-methyl-(R,R)-l,2-butanediol

The substantially same method as described in Preparation Example 16 was conducted, except that l-(2,4-dichlorophenyl)-3 -methyl-trans- l-butene(Preparation Example 7) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.26g, yield 60-95%).

1H NMPv(400MHz, CDC1 ₃ ) 51.00(d, J=6.8Hz, 6H), 1.60~1.65(m, 1H), 2.35(d, J=4.0Hz, 1H), 3.12(d, J=8.4Hz, 1H), 4.13~4.18(m, 1H), 5.36(t, J=7.6Hz, 1H), 7.17~7.35(m, 3H)

Preparation Example 35: Synthesis of l-(2,4-dichlorophenyl)-(S,S)-l,2-hexanediol The substantially same method as described in Preparation Example 14 was conducted, except that l-(2,4-dichlorophenyl)-trans-l-propene(Preparation Example 8) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (l .lg, yield 60-90%).

Ή NMR(400MHz, CDC1 ₃ ) 50.89~0.93(m, 3H), 1.30~1.39(m, 2H), 1.49~1.52(m, 2H), 1.56~1.62(m, 2H), 2.05(d, J=5.2Hz, 1H), 2.74(d, J=5.2Hz, 1H), 3.72~3.77(m, 1H), 4.98(t, J=4.8Hz, 1H), 7.28~7.50(m, 3H)

Preparation Example 36: Synthesis of l-(2,4-dich!orophenyl)-(R,R)-l,2-hexanediol

The substantially same method as described in Preparation Example 15 was conducted, except that l-(2,4-dichlorophenyl)-trans-l-propene(Preparation Example 8) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (1.2g, yield 60-95%).

l NMR(400MHz, CDC1 ₃ ) 60.89~0.93(m, 3H), 1.30~1.39(m, 2H), 1.49~1.52(m, 2H), 1.56~1.62(m, 2H), 2.05(d, J=5.2Hz, 1H), 2.74(d, J=5.2Hz, 1H), 3.72~3.77(m, 1H), 4.98(t, J=4.8Hz, 1H), 7.28~7.50(m, 3H)

Preparation Example 37: Synthesis of the mixture of l-(2,4-dichlorophenyl)-(S,S)- 1,2-hexanedioI and l-(2,4-dichlorophenyl)-(R,R)-l,2-hexanediol

The substantially same method as described in Preparation Example 16 was conducted, except that l-(2,4-dichlorophenyl)-trans-l-propene(Preparation Example 8) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.67g, yield 60-95%).

1H NMR(400MHz, CDC1 ₃ ) 60.89~0.93(m, 3H), 1.30~1.39(m, 2H), 1.49~1.52(m, 2H), 1.56~1.62(m, 2H), 2.05(d, J=5.2Hz, 1H), 2.74(d, J=5.2Hz, 1H), 3.72~3.77(m, 1H), 4.98(t, J=4.8Hz, 1H), 7.28~7.50(m, 3H)

Preparation Example 38: Synthesis of l-(2,6-dichIorophenyl)-(S,S)-l,2-propanediol

The substantially same method as described in Preparation Example 14 was conducted, except that l-(2,6-dichlorophenyl)-trans-l-propene(Preparation Example 9) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.9g, yield 60-90%).

1H NMR(400MHz, CDC1 ₃ ) 61.10(d, J=6.4Hz, 3H), 2.72(d, J=2.4Hz, 1H), 3.10(d, J=8.4Hz, 1H), 4.47~4.54(m, 1H), 5.24(t, J=8.8Hz, 1H), 7.18~7.36(m, 3H)

Preparation Example 39: Synthesis of l-(2,6-dichlorophenyl)-(R,R)-l,2-propanediol

The substantially same method as described in Preparation Example 15 was conducted, except that l-(2,6-dichlorophenyl)-trans-l-propene(Preparation Example 9) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.84g, yield 60-90%).

1H NMR(400MHz, CDC1 ₃ ) 61.10(d, J=6.4Hz, 3H), 2.72(d, J=2.4Hz, 1H), 3.10(d, J=8.4Hz, 1H), 4.47~4.54(m, 1H), 5.24(t, J=8.8Hz, 1H), 7.18~7.36(m, 3H)

Preparation Example 40: Synthesis of the mixture of l-(2,6-dichlorophenyl)-(S,S)- 1,2-propanediol and l-(2,6-dichlorophenyl)-(R,R)-l,2-propanediol

The substantially same method as described in Preparation Example 16 was conducted, except that l-(2,6-dichlorophenyl)-trans-l-propene(Preparation Example 9) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.9 lg, yield 60-90%).

1H NMR(400MHz, CDC1 ₃ ) 61.10(d, J=6.4Hz, 3H), 2.72(d, J=2.4Hz, 1H), 3.10(d, J=8.4Hz, 1H), 4.47~4.54(m, 1H), 5.24(t, J=8.8Hz, 1H), 7.18~7.36(m, 3H)

Preparation Example 41: Synthesis of l-(2,6-dichIorophenyI)-(S,S)-l,2-butanediol

The substantially same method as described in Preparation Example 14 was conducted, except that l-(2,6-dichlorophenyl)-trans-l-butene(Preparation Example 10) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (1.23g, yield 60-95%).

1H NMR(400MHz, CDC1 ₃ ) 60.97(t, J=7.6Hz, 3H), 1.26~1.53(m, 2H), 2.64(dd, J=0.8Hz, J=4.0Hz, 1H), 3.14(d, J=8.4Hz, 1H), 4.22~4.26(m, 1H), 5.26(t, J=8.4Hz, 1H), 7.17~7.35(m, 3H)

Preparation Example 42: Synthesis of l-(2,6-dichlorophenyl)-(R,R)-l,2-butanediol

The substantially same method as described in Preparation Example 15 was conducted, except that l-(2,6-dichlorophenyl)-trans-l-butene(Preparation Example 10) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.96g, yield 60-95%).

Ή NMR(400MHz, CDC1 ₃ ) 60.97(t, J=7.6Hz, 3H), 1.26~1.53(m, 2H), 2.64(dd, J=0.8Hz, J=4.0Hz, 1H), 3.14(d, J=8.4Hz, 1H), 4.22~4.26(m, 1H), 5.26(t, J=8.4Hz, 1H), 7.17~7.35(m, 3H)

Preparation Example 43: Synthesis of the mixture of l-(2,6-dichlorophenyl)-(S,S)- 1,2-butanediol and l-(2,6-dichlorophenyl)-(R,R)-l,2-butanediol

The substantially same method as described in Preparation Example 16 was conducted, except that l-(2,6-dichlorophenyl)-trans-l-butene(Preparation Example 10) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.86g, yield 60-95%).

1H NMR(400MHz, CDC1 ₃ ) 50.97(t, J=7.6Hz, 3H), 1.26~1.53(m, 2H), 2.64(dd, J=0.8Hz, J=4.0Hz, 1H), 3.14(d, J=8.4Hz, 1H), 4.22~4.26(m, 1H), 5.26(t, J=8.4Hz, 1H), 7.17~7.35(m, 3H)

Preparation Example 44: Synthesis of l-(2,6-dichlorophenyl)-3-methyl-(S,S)-l,2- butanediol

The substantially same method as described in Preparation Example 14 was conducted, except that l-(2,6-dichlorophenyl)-3 -methyl-trans- l-butene(Preparation Example 11) was used instead of l-(2-chlorophenyl)-trans-l -propene(Preparation Example 1), to obtain the title compound (0.25g, yield 60-95%).

1H NMR(400MHz, CDC1 ₃ ) 51.00(d, J=6.8Hz, 6H), 1.60~1.65(m, 1H), 2.35(d, J-4.0Hz, 1H), 3.12(d, J=8.4Hz, 1H), 4.13~4.18(m, 1H), 5.36(t, J=7.6Hz, 1H), 7.17~7.35(m, 3H)

Preparation Example 45: Synthesis of l-(2,6-dichlorophenyl)-3-methyl-(R,R)-l,2- butanediol

The substantially same method as described in Preparation Example 15 was conducted, except that l-(2,6-dichlorophenyl)-3 -methyl-trans- l-butene(Preparation Example 11) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.37g, yield 60-95%). 1H NMR(400MHz, CDC1 ₃ ) 51.00(d, J=6.8Hz, 6H), 1.60~1.65(m, 1H), 2.35(d, J=4.0Hz, 1H), 3.12(d, J=8.4Hz, 1H), 4.13~4.18(m, 1H), 5.36(t, J=7.6Hz, 1H), 7.17~7.35(m, 3H)

Preparation Example 46: Synthesis of the mixture of l-(2,6-dichlorophenyl)-3- methyl- -l,2-butanediol and l-(2,6-dichlorophenyl)-3-methyl-(R,R)-l,2-butanediol

The substantially same method as described in Preparation Example 16 was conducted, _, except that l-(2,6-dichlorophenyl)-3 -methyl-trans- l-butene(Preparation Example 11) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.47g, yield 60-95%).

1H NMR(400MHz, CDC1 ₃ ) 61.00(d, J=6.8Hz, 6H), 1.60~1.65(m, 1H), 2.35(d, J=4.0Hz, 1H), 3.12(d, J=8.4Hz, 1H), 4.13~4.18(m, 1H), 5.36(t, J=7.6Hz, 1H), 7.17~7.35(m, 3H)

Preparation Example 47: Synthesis of l-(2,6-dichlorophenyl)-(S,S)-l,2-hexanediol

The substantially same method as described in Preparation Example 14 was conducted, except that l-(2,6-dichlorophenyl)-trans-l-hexene(Preparation Example 12) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.36g, yield 60-90%).

1H NMR(400MHz, CDC1 ₃ ) 60.85(t, J=6.8Hz, 3H), 1.20~1.31(m, 4H), 1.45~1.53(m, 2H), 2.61~2.62(m, 1H), 3.12(d, J=8.4Hz, 1H), 4.28~4.33(m, 1H), 5.25(t, J=8.4Hz, 1H), 7.18~7.35(m, 3H)

Preparation Example 48: Synthesis of l-(2,6-dichlorophenyl)-(R,R)-l,2-hexanediol The substantially same method as described in Preparation Example 15 was conducted, except that l-(2,6-dichlorophenyl)-trans-l-hexene(Preparation Example 12) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.58g, yield 60-90%).

1H NMR(400MHz, CDC1 ₃ ) 60.85(t, J=6.8Hz, 3H), 1.20-1.3 l (m, 4H), 1.45~1.53(m, 2H), 2.61~2.62(m, 1H), 3.12(d, J=8.4Hz, 1H), 4.28~4.33(m, 1H), 5.25(t, J=8.4Hz, 1H), 7.18~7.35(m, 3H)

Preparation Example 49: Synthesis of the mixture of l-(2,6-dichlorophenyl)-(S,S)- 1,2-hexanediol and l-(2,6-dichlorophenyl)-(R,R)-l,2-hexanediol

The substantially same method as described in Preparation Example 16 was conducted, except that l-(2,6-dichlorophenyl)-trans-l-hexene(Preparation Example 12) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.62g, yield 60-90%).

1H NMPv(400MHz, CDC1 ₃ ) 60.85(t, J=6.8Hz, 3H), 1.20-1.3 l(m, 4H), 1.45-1.53(m, 2H), 2.61~2.62(m, 1H), 3.12(d, J=8.4Hz, 1H), 4.28~4.33(m, 1H), 5.25(t, J=8.4Hz, 1H), 7.18~7.35(m, 3H)

Preparation Example 50: Synthesis of methyl 2-(2-chlorophenyl)-(R)-2- hydroxyacetate

15g of (R)-2-chloromandelic acid was mixed with methanol (CH ₃ OH, 150ml) and phosphorus chloride oxide (POCl ₃ , 0.76ml) in a flask by stirring using a magnetic stirrer at the room temperature for 6 hours. When the reaction was completed, the obtained product was washed with an aqueous solution of sodium sulfite (Na ₂ S0 ₃ ) and ethylacetate (EA). Then, the organic layer was dehydrated with anhydrous magnesium sulfate (MgS0 ₄ ), filtrated, and concented under reduced pressure. The concentrated residue was purified by a silica gel column chromatography to produce the title compound (15.64g, yield 95%).

1H NMR(400MHz, CDC1 ₃ ) δ 3.59(d, J=5.2, 1H), 3.79(t, J=6.0, 3H), 5.59(d, J=5.2, 1H), 7.28~7.43(m, 4H)

Preparation Example 51: Synthesis of 2-(2-chlorophenyl)-(R)-2-hydroxy-N- methoxy-N-methylacetamide

Ν,Ο-dimethylhydroxylamine hydrochloride (Ν,Ο-dimethylhydroxylamine.HCl, 15.2g) was dissolved in dichloromethane (DCM, 150ml), and cooled to 0 ^° C using an ice-bath. Then, 77.7ml of 2.0M trimethylaluminium in hexane was slowly added thereto in drop- wise manner for 30 minutes. Thereafter, the ice-bath was removed, and the obtained product was stirred at the room temperature for 2 hours. Methyl-2-(2-chlorophenyl)-(R)-2-hydroxyacetate(15.64g) dissolved in dichloromethane(DCM, 150ml) was added in drop-wise manner thereto at the room temperature for 30 minutes, and subjected to reflux for 12 hours. When the reaction was completed, the obtained product was cooled to 0 ^° C , and washed by a slow drop- wise addition of hydrochloric acid (HC1, 200ml). The obtained organic layer was washed with distilled water and brine, dehydrated with anhydrous magnesium sulfate (MgS0 ₄ ), filtrated, and concented under reduced pressure. The concentrated residue was purified by a silica gel column chromatography to produce the title compound (14.68g, yield 82%).

1H NMR(400MHz, CDC1 ₃ ) 53.23(s, 3H), 3.28(s, 3H), 4.33(d, J=6.0Hz, 1H), 5.81(d, J=5.6Hz, 1H), 7.23~7.42(m, 4H)

Preparation Example 52: Synthesis of 2-(2-chlorophenyl)-N-methoxy-(R)-2- (methoxymethoxy)-N-methylacetamide

2-(2-chlorophenyl)-(R)-2-hydroxy-N-methoxy-N-methylacetamide (14.68g) obtained in Preparation Example 51 was dissolved in dichloromethane (DCM, 140ml), and cooled to 0 ^° C . Diisopropylethylamine (55.67ml) was slowly added thereto in drop-wise manner, and stirred for 10 minutes. Chloro methyl methyl ether (25.25ml) was slowly added thereto in drop- wise manner for 30 minutes. After 30 minutes, the ice-bath was removed and the obtained product was stirred for 30 at room temperature. When the reaction was completed, the obtained product was cooled to 0 ^° C . And then, to the obtained product, 1M sodium hydroxide solution (1M NaOH, 20ml) was added in drop-wise manner, and dichloromethane(DMC) was injected. Then the obtained product was washed with water. The obtained organic layer was dehydrated with anhydrous magnesium sulfate (MgSC ), filtrated, and concented under reduced pressure. The concentrated residue was purified by a silica gel column chromatography to produce the title compound (15.57g, yield 89%).

1H NMR(400MHz, CDC1 ₃ ) 63.19(s, 3H), 3.42(s, 3H), 3.47(s, 3H), 4.75(d, J=6.8, 1H), 4.81(d, J=6.8, 1H), 6.07(s, 1H), 7.27~7.58(m, 4H)

Preparation Example 53: Synthesis of l-(2-chIorophenyl)-(R)-l- (methoxy methoxy)prop ane-2-on

2-(2-chlorophenyl)-N-methoxy-(R)-2-(methoxymethoxy)-N-methyl acetamide( 15.57g) obtained in Preparation Example 52 was dissolved in tetrahydrofuran(THF, 150ml), and cooled to 0 ^° C . 3.0M methyl magnesium bromide (MeMgBr) solution in ether was added thereto in drop- wise manner for 30 minutes, and the obtained product was stirred for 1 hour at 0 ^° C . When the reaction was completed, diethyl ether( 100ml) was added thereto. The obtained product was washed with 10%(w/v) potassium hydrogen sulfate (KHS0 _4; 100ml) and then, washed again with brine. The obtained organic layer was dehydrated with anhydrous magnesium sulfate (MgS0 ₄ ), filtrated, and concented under reduced pressure. The concentrated residue was purified by a silica gel column chromatography to produce the title compound (11.83g, yield 90%).

1H NMR(400MHz, CDC1 ₃ ) 52.18(s, 3H), 3.39(s, 3H), 4.65(d, J=6.8, 1H), 4.74(d, J=6.8, 1H), 5.63(s, 1H), 7.30~7.45(m, 4H)

Preparation Example 54: Synthesis of l-(2-chlorophenyl)-(R)-l-(methoxymethoxy)- (S)-2-propanoI

1 -(2-chlorophenyl)-(R)- 1 -(methoxymethoxy)propane-2-on( 11.83 g) obtained in Preparation Example 53 was dissolved in toluene( 110ml), and cooled to -40 ^° C . Sodium bis(2- methoxyethoxy)aluminumhydride solution (15.7ml) in toluene was slowly added thereto for 30 minutes, and then, the obtained product was stirred for 1 hour. When the reaction was completed, the obtained product was washed by slow drop-wise addition of sodium potassium tartrate (100ml). The obtained organic layer was dehydrated with anhydrous magnesium sulfate (MgS0 ₄ ), filtrated, and concented under reduced pressure. The concentrated residue was purified by a silica gel column chromatography to produce the title compound (10.38g, yield 87%).

1H NMR(400MHz, CDC1 ₃ ) 61.13(d, J=6.4, 3H), 2.33(d, J=7.2, 1H), 3.44(s, 3H), 4.10~4.18(m, 1H), 4.61(d, J=6.4, 1H), 4.69(d, J=6.8, 1H), 5.14(d, J=3.6, 1H), 7.22~7.55(m, 4H)

Preparation Example 55: Synthesis of l-(2-chlorophenyl)-(R,S)-l,2-propanediol

1 -(2-chlorophenyl)-(R)- 1 -(methoxymethoxy)-(S)-2-propanol(l 0.38g) obtained in Preparation Example 54 was dissolved in methanol (CH ₃ OH, 100ml), and then, cooled to 0 ^° C . 8M hydrochloric acid(HCl, 56.2ml) was slowly added in drop-wise manner to the obtained product, and then, the obtained product was warmed to the room temperature, and stirred for 15 hours. When the reaction was completed, the obtained product was cooled to 0 ^° C . 5N sodium hydroxide (NaOH, 30ml) was slowly added thereto, and the obtained product was subjected to vacuum concentration. The obtained product was diluted with ethylacetate. The obtained organic layer was washed with distilled water, dehydrated with anhydrous magnesium sulfate (MgS0 ₄ ), filtrated, and concented under reduced pressure. The concentrated residue was purified by a silica gel column chromatography to produce the title compound (7.05g, yield 60-90%).

Ή NMR(400MHz, CDC1 ₃ ) 61.07(d, J=6.8, 3H), 2.01(d, J=5.6, 1H), 2.61(s, 1H), 4.21~4.27(m, 1H), 5.24(d, J=3.6, 1H), 7.22~7.64(m, 4H)

Preparation Example 56: Synthesis of l-(2-chlorophenyl)-(S,R)-l,2-propanediol

The substantially same method as described in Preparation Example 50-55 was conducted, except that (S)-2-chloromandelic acid was used instead of (R)-2-chloromandelic acid, to obtain the title compound (5.04g, yield 84%).

1H NMR(400MHz, CDC1 ₃ ) 51.07(d, J=6.8, 3H), 2.00(d, J=5.6, 1H), 2.54(d, J=3.6, 1H), 4.22~4.26(m, 1H), 5.25(t, J=3.2, 1H), 7.22~7.65(m, 4H)

Preparation Example 57: Synthesis of l-(2,3-dichlorophenyl)-(S,S)-l,2-propanediol

The substantially same method as described in Preparation Example 14 was conducted, except that l-(2,3-dichlorophenyl)-trans-l-propene(Preparation Example 13) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.9g, yield 60-90%).

Ή NMR(400MHz, CDC1 ₃ ) 61.10(d, J=6.4Hz, 3H), 2.72(d, J=2.4Hz, 1H), 3.10(d, J=8.4Hz, 1H), 4.47~4.54(m, 1H), 5.24(t, J=8.8Hz, 1H), 7.18- (m, 3H)

Preparation Example 58: Synthesis of l-(2,3-dichlorophenyl)-(R,R)-l,2-propanediol The substantially same method as described in Preparation Example 15 was conducted, except that l-(2,3-dichlorophenyl)-trans-l-propene(Preparation Example 13) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.84g, yield 60-90%).

1H NMR(400MHz, CDC1 ₃ ) 61.10(d, J=6.4Hz, 3H), 2.72(d, J=2.4Hz, 1H), 3.10(d, J=8.4Hz, 1H), 4.47~4.54(m, 1H), 5.24(t, J=8.8Hz, 1H), 7.18- (m, 3H)

Preparation Example 59: Synthesis of the mixture of l-(2,3-dichlorophenyl)-(S,S)- 1,2-propanediol and l-(2,3-dichlorophenyl)-(R,R)-l,2-propanediol

The substantially same method as described in Preparation Example 16 was conducted, except that l-(2,3-dichlorophenyl)-trans-l-propene(Preparation Example 13) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.91 g, yield 60-90%).

1H NMR(400MHz, CDC1 ₃ ) 61.10(d, J=6.4Hz, 3H), 2.72(d, J=2.4Hz, 1H), 3.10(d, J=8.4Hz, 1H), 4.47~4.54(m, 1H), 5.24(t, J=8.8Hz, 1H), 7.18~(m, 3H)

Preparation Example 60: Synthesis of l-(2-fluorophenyl)-trans-l-propene

The substantially same method as described in Preparation Example 1 was conducted, except that 2-fiuorobenzenaldehyde was used instead of 2-chlorobenzenealdehyde, to obtain the title compound (6.67g, yield 61%).

1H NMR(400MHz, CDCI3) 61.94(d, J=6.8Hz, 3H), 6.30-6.38(m, 1H), 6.57(d, J=16Hz, 1H), 7.00-7.4 l(m, 4H)

Preparation Example 61: Synthesis of l-(2-fluorophenyl)-(S,S)-l,2-propanediol

The substantially same method as described in Preparation Example 14 was conducted, except that l-(2-fluorophenyl)-trans-l-propene (Preparation Example 60) was used instead of 1- (2-chlorophenyl)-trans-l-propene (Preparation Example 1), to obtain the title compound (6.46g, yield 78%).

1H NMR(400MHz, CDC1 ₃ ) 61.15(d, J=6.4Hz, 3H), 2.43(d, J=3.6Hz, 1H), 2.69(d, J=4.8Hz, 1H), 3.90~3.98(m, 1H), 4.78(dd, J=4.4, 7.2Hz, 1H), 7.04~7.50(m, 4H)

Preparation Example 62: Synthesis of l-(2-fiuorophenyl)-(R,R)-l,2-propanediol

The substantially same method as described in Preparation Example 15 was conducted, except that l-(2-fluorophenyl)-trans-l-propene (Preparation Example 60) was used instead of 1- (2-chlorophenyl)-trans-l-propene (Preparation Example 1), to obtain the title compound (3.29g, yield 79%).

1H NMR(400MHz, CDC1 ₃ ) 51.15(d, J=6.4Hz, 3H), 2.43(d, J=3.6Hz, 1H), 2.69(d, J=4.8Hz, 1H), 3.90~3.98(m, 1H), 4.78(dd, J=4.4, 7.2Hz, 1H), 7.04~7.50(m, 4H)

Preparation Example 63: Synthesis of 2-iodobenzenealdehyde

In a flask, 2-iodobenzyl alcohol (4g, 17.09mmol) was dissolved in dichloromethane (MC, 85ml), and then, manganese oxide (Mn0 ₂ , 14.86g, 170.92mmol) was added thereto. The obtained reaction product was stirred under the reflux condition. When the reaction was completed, the obtained reaction product was cooled to the room temperature, and then, fiteated and concentrated using celite, to obtain the title compound (3.6g, yield 91%).

1H NMPv(400MHz, CDCl ₃ )57.30~7.99(m, 4H), 10.10(s, 1H) Preparation Example 64: Synthesis of l-(2-iodophenyl)-trans-l-propene

The substantially same method as described in Preparation Example 1 was conducted, except that 2-iodobenzenealdehyde (Preparation Example 63) was used instead of 2- chlorobenzenealdehyde, to obtain the title compound (3.4g, yield 65%).

1H NMR(400MHz, CDCl ₃ )51.95(dd, J=6.8Hz, 1.6Hz, 3H), 6.09-6.18(m, 1H), 6.60(dd, J=15.66Hz, 1.8Hz, 1H), 6.89~7.84(m, 4H)

Preparation Example 65: Synthesis of l-(2-iodophenyl)-trans-l-butene

The substantially same method as described in Preparation Example 64 was conducted, except that 3-heptanone was used instead of 3-pentanone, to obtain the title compound (8.5g, yield 75%).

1H NMR(400MHz, CDCl ₃ )51.46(t, J=7.6Hz, 3H), 2.26~2.34(m, 2H), 6.17(dt, J=15.6Hz, 6.6Hz 1H), 6.57(d, J=15.6Hz, 1H), 6.89~7.85(m, 4H)

Preparation Example 66: Synthesis of l-(2-iodophenyl)-(S,S)-l,2-propanediol

The substantially same method as described in Preparation Example 14 was conducted, except that l-(2-iodophenyl)-trans-l-propene (Preparation Example 64) was used instead of l-(2- chlorophenyl)-trans-l-propene (Preparation Example 1), to obtain the title compound (3.4g, yield 88%).

l NMR(400MHz, CDCl ₃ )51.27(d, J=6.4Hz, 3H), 2.26(br s, 1H), 2.74(br s, 1H), 3.99(t, J=6.0Hz, 1H), 4.81(d, J=4.0Hz, 1H), 7.01~7.87(m, 4H)

Preparation Example 67: Synthesis of l-(2-iodorophenyl)-(R,R)-l,2rpropanediol

The substantially same method as described in Preparation Example 15 was conducted was conducted, except that l-(2-iodophenyl)-trans-l-propene (Preparation Example 64) was used instead of l-(2-chlorophenyl)-trans-l-propene (Preparation Example 1), to obtain the title compound (7.4g, yield 84%).

Ή NMR(400MHz, CDCl ₃ )51.26(d, J=6.4Hz, 3H), 2.35(br s, 1H), 2.85(br d, J=4.0Hz, 1H), 3.98(t, J=6.2Hz, 1H), 4.80(dd, J=5.0, 4.4Hz, 1H), 7.00~7.87(m, 4H)

Preparation Example 68: Synthesis of l-(2- iodophenyl)-(S,S)-l,2-butanediol

The substantially same method as described in Preparation Example 14 was conducted was conducted, except that l-(2-iodophenyl)-trans-l-butene (Preparation Example 65) was used instead of l-(2-chlorophenyl)-trans-l-propene (Preparation Example 1), to obtain the title compound (9.5g, yield 84%).

1H NMR(400MHz, CDCl ₃ )81.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 2.07(br s, 1H), 2.74(br s, 1H), 3.71~3.76(m, 1H), 4.87(d, J=4.8Hz, 1H), 7.01~7.87(m, 4H)

Preparation Example 69: Synthesis of l-(2- iodophenyl)-(R,R)-l,2-butanediol

The substantially same method as described in Preparation Example 15 was conducted, except that l-(2-iodophenyl)-trans-l-butene (Preparation Example 65) was used instead of l-(2- chlorophenyl)-trans-l-propene (Preparation Example 1), to obtain the title compound (1.9g, yield 70-90%).

1H NMR(400MHz, CDC1 ₃ ) 61.01(t, J=7.4Hz, 3H), 1.52~1.65(m, 2H), 2.01(d, J=4.4Hz, 1H), 2.74(d, J=5.2Hz, 1H), 3.69~3.75(m, 1H), 5.05(t, J=5.0Hz, 1H), 7.03~7.84(m, 4H)

Preparation Example 70: Synthesis of l-(2-iodophenyl)-3-methyl-trans-l-butene

The substantially same method as described in Preparation Example 3 was conducted, except that 2-iodobenzenaldehyde was used instead of 2-chlorobenzenaldehyde, to obtain the title compound (0.37g, yield 10-40%).

l NMR(400MHz, CDC1 ₃ ) 61.14(d, J=6.8Hz, 6H), 2.25~2.57(m, 1H), 6.20(dd, J=16Hz, 7.2Hz, 1H), 7.64(d, J=16Hz, 1H), 7.04~7.82(m, 4H)

Preparation Example 71: Synthesis of l-(2-iodophenyl)-trans-l-hexene

The substantially same method as described in Preparation Example 4 was conducted, except that 2-iodobenzenaldehyde was used instead of 2-chlorobenzenaldehyde, to obtain the title compound (1.21g, yield 10-40%).

1H NMR(400MHz, CDC1 ₃ ) 50.96(t, J=7.2Hz, 3H), 1.33~1.56(m, 4H), 2.26~2.32(m, 4H), 6.24(dt, J=l 5.6Hz, 7Hz, 1H), 6.78(d, J=16Hz, 1H), 7.12~7.51(m, 4H)

Preparation Example 72: Synthesis of l-(2-fluorophenyl)-trans-l-butene

The substantially same method as described in Preparation Example 2 was conducted, except that 2-fluorobenzenaldehyde was used instead of 2-chlorobenzenaldehyde, to obtain the title compound (0.72g, yield 10-40%).

Ή NMR(400MHz, CDC1 ₃ ) 61.14(d, J=7.6Hz, 3H), 2.29~2.33(m, 2H), 6.28(dt, J=16Hz, 6.4Hz, 1H), 6.78(d, J=l 5.6Hz, 1H), 7.15~7.55(m, 4H) Preparation Example 73: Synthesis of l-(2-fluorophenyl)-3-methyl-trans-l-butene

The substantially same method as described in Preparation Example 3 was conducted, except that 2-fluorobenzenaldehyde was used instead of 2-chlorobenzenaldehyde, to obtain the title compound (1.31g, yield 10-40%).

1H NMR(400MHz, CDC1 ₃ ) 61.14(d, J=6.8Hz, 6H), 2.25~2.57(m, 1H), 6.20(dd, J=16Hz, 7.2Hz, 1H), 7.64(d, J=16Hz, 1H), 7.11~7.55(m, 4H)

Preparation Example 74: Synthesis of l-(2-fluorophenyl)-trans-l-hexene

The substantially same method as described in Preparation Example 4 was conducted, except that 2-fluorobenzenaldehyde was used instead of 2-chlorobenzenaldehyde, to obtain the title compound (1.02g, yield 10-40%).

1H NMPv(400MHz, CDC1 ₃ ) 50.96(t, J=7.2Hz, 3H), 1.33~1.56(m, 4H), 2.26~2.32(m, 4H), 6.24(dt, J=l 5.6Hz, 7Hz, 1H), 6.78(d, J=16Hz, 1H), 7.14-7:52(m, 4H)

Preparation Example 75: Synthesis of l-(3-iodophenyl)-trans-l-propene

The substantially same method as described in Preparation Example 64 was conducted, except that 3-iodobenzenaldehyde was used instead of 2-iodobenzenaldehyde, to obtain the title compound (1.22g, yield 10-40%).

1H NMR(400MHz, CDCl ₃ )61.95(dd, J=6.8Hz, 1.6Hz, 3H), 6.09-6.18(m, 1H), 6.60(dd, J=l 5.66Hz, 1.8Hz, 1H), 6.87~7.80(m, 4H)

Preparation Example 76: Synthesis of l-(3-iodophenyl)-trans-l-butene The substantially same method as described in Preparation Example 65 was conducted, except that 3-iodobenzenaldehyde was used instead of 2-iodobenzenaldehyde, to obtain the title compound (1.12g, yield 10-40%).

1H NMR(400MHz, CDCl ₃ )51.46(t, J=7.6Hz, 3H), 2.26~2.34(m, 2H), 6.17(dt, J=15.6Hz, 6.6Hz 1H), 6.57(d, J=15.6Hz, 1H), 6.86~7.81(m, 4H)

Preparation Example 77: Synthesis of l-(3-iodophenyl)-3-methyl-trans-l-butene

The substantially same method as described in Preparation Example 70 was conducted, except that 3-iodobenzenaldehyde was used instead of 2-iodobenzenaldehyde, to obtain the title compound (0.62g, yield 10-40%).

Ή NMR(400MHz, CDC1 ₃ ) 61.14(d, J=6.8Hz, 6H), 2.25~2.57(m, 1H), 6.20(dd, J=16Hz, 7.2Hz, 1H), 7.64(d, J=16Hz, 1H), 6.88~7.64(m, 4H)

Preparation Example 78: Synthesis of l-(3-iodophenyl)-trans-l-hexene

The substantially same method as described in Preparation Example 71 was conducted, except that 3-iodobenzenaldehyde was used instead of 2-iodobenzenaldehyde, to obtain the title compound (0.42g, yield 10-40%).

1H NMR(400MHz, CDC1 ₃ ) 50.96(t, J=7.2Hz, 3H), 1.33-1.56(m, 4H), 2.26~2.32(m, 4H), 6.24(dt, J=15.6Hz, 7Hz, 1H), 6.78(d, J=16Hz, 1H), 6.88-7.59(m, 4H)

Preparation Example 79: Synthesis of l-(4-fluorophenyl)-trans-l-propene

The substantially same method as described in Preparation Example 60 was conducted, except that 4-fluorobenzenaldehyde was used instead of 2-fluorobenzenaldehyde, to obtain the title compound (0.29g, yield 10-40%).

1H NMR(400MHz, CDC1 ₃ ) 51.94(d, J=6.8Hz, 3H), 6.30~6.38(m, 1H), 6.57(d, J=16Hz, 1H), 6.85~7.04(m, 4H)

Preparation Example 80: Synthesis of l-(4-fluorophenyI)-trans-l-butene

The substantially same method as described in Preparation Example 72 was conducted, except that 4-fluorobenzenaldehyde was used instead of 2-fluorobenzenaldehyde, to obtain the title compound (1.03g, yield 10-40%).

1H NMR(400MHz, CDC1 ₃ ) 51.14(d, J=7.6Hz, 3H), 2.29~2.33(m, 2H), 6.28(dt, J=16Hz, 6.4Hz, 1H), 6.78(d, J=15.6Hz, 1H), 6.88.15~7.05(m, 4H)

Preparation Example 81: Synthesis of l-(4-fluorophenyl)-3-methyl-trans-l-butene

The substantially same method as described in Preparation Example 73 was conducted, except that 4-fluorobenzenaldehyde was used instead of 2-fluorobenzenaldehyde, to obtain the title compound ( 1.41 g, yield 10-40%)

1H NMR(400MHz, CDC1 ₃ ) 61.14(d, J=6.8Hz, 6H), 2.25~2.57(m, 1H), 6.20(dd, J=16Hz, 7.2Hz, 1H), 7.64(d, J=16Hz, 1H), 6.83~7.09(m, 4H)

Preparation Example 82: Synthesis of l-(4-fluorophenyl)-trans-l-hexene

The substantially same method as described in Preparation Example 74 was conducted, except that 4-fluorobenzenaldehyde was used instead of 2-fluorobenzenaldehyde, to obtain the title compound (0.43g, yield 10-40%)

1H NMR(400MHz, CDC1 ₃ ) 50.96(t, J=7.2Hz, 3H), 1.33-1.56(m, 4H), 2.26~2.32(m, 4H), 6.24(dt, J=15.6Hz, 7Hz, 1H), 6.78(d, J=16Hz, 1H), 6.84~7.07(m, 4H)

Preparation Example 83: Synthesis of l-(2- iodophenyl)-3-methyl-(S,S)-l,2- butanediol

The substantially same method as described in Preparation Example 14 was conducted, except that 1 -(2 -iodophenyl)-3 -methyl-trans- 1 -butene(Preparation Example 70) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.52g, yield 60-90%).

1H NMR(400MHz, CDC1 ₃ ) 61.07(t, J=7.2Hz, 6H), 1.83~1.89(m, 1H), 1.92(d, J=5.6Hz, 1H), 2.69(d, J=6.4Hz, 1H), 3.53~3.56(m, 1H), 5.22~5.25(m, 1H), 7.04~7.85(m, 4H)

Preparation Example 84: Synthesis of l-(2- iodophenyl)-3-methyl-(R,R)-l,2- butanediol

The substantially same method as described in Preparation Example 15 was conducted, except that l-(2-iodophenyl)-trans-l-butene(Preparation Example 65) was used instead of l-(2- chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.52g, yield 60-90%)

Ή NMR(400MHz, CDCl ₃ )61.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 2.07(br s, 1H), 2.74(br s, 1H), 3.71~3.76(m, 1H), 4.87(d, J=4.8Hz, 1H), 7.01~7.87(m, 4H)

Preparation Example 85: Synthesis of l-(2- iodophenyl)-(S,S)-l,2-hexanediol

The substantially same method as described in Preparation Example 14 was conducted, except that l-(2-iodophenyl)-trans-l-hexene(Preparation Example 71) was used instead of l-(2- chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (1.21g, yield 60-90%) 1H NMR(400MHz, CDC1 ₃ ) 60.90(t, J=7.2Hz, 3H), 1.35~1.65(m, 6H), 2.08(d, J=4.4Hz, 1H), 2.71(d, J=5.2Hz, 1H), 3.78~3.83(m, 1H), 5.04(t, J=5.0Hz, 1H), 7.02~7.79(m, 4H)

Preparation Example 86: Synthesis of l-(2- iodophenyI)-(R,R)-l,2-hexanedioi

The substantially same method as described in Preparation Example 15 was conducted, except that l-(2-iodophenyl)-trans-l-hexene(Preparation Example 71) was used instead of l-(2- chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (0.74g, yield 60-90%)

1H NMR(400MHz, CDC1 ₃ ) 50.90(t, J=7.2Hz, 3H), 1.35~1.65(m, 6H), 2.08(d, J=4.4Hz, 1H), 2.71(d, J=5.2Hz, 1H), 3.78~3.83(m, 1H), 5.04(t, J=5.0Hz, 1H), 7.02~7.79(m, 4H)

Preparation Example 87: Synthesis of l-(3-iodophenyl)-(S,S)-l,2-propanediol

The substantially same method as described in Preparation Example 66 was conducted, except that l-(3-iodophenyl)-trans-l-propene (Preparation Example 75) was used instead of l-(2- iodophenyl)-trans-l-propene (Preparation Example 64), to obtain the title compound (2.03g, yield 60-90%).

Ή NMR(400MHz, CDCl ₃ )51.27(d, J=6.4Hz, 3H), 2.26(br s, 1H), 2.74(br s, 1H), 3.99(t, J=6.0Hz, 1H), 4.81(d, J=4.0Hz, 1H), 6.98~7.50(m, 4H)

Preparation Example 88: Synthesis of l-(3-iodophenyl)-(R,R)-l,2-propanediol

The substantially same method as described in Preparation Example 67 was conducted, except that l-(3-iodophenyl)-trans-l-propene (Preparation Example 75) was used instead of l-(2- iodophenyl)-trans-l -propene (Preparation Example 64), to obtain the title compound (1.12g, yield 60-90%).

1H NMR(400MHz, CDCl ₃ )51.27(d, J=6.4Hz, 3H), 2.26(br s, 1H), 2.74(br s, 1H), 3.99(t, J=6.0Hz, 1H), 4.8 l(d, J=4.0Hz, 1H), 6.98~7.50(m, 4H)

Preparation Example 89: Synthesis of l-(3-iodophenyl)-(S,S)-l,2-butanediol

The substantially same method as described in Preparation Example 68 was conducted, except that l-(3-iodophenyl)-trans-l-butene (Preparation Example 76) was used instead of l-(2- iodophenyl)-trans-l-propene (Preparation Example 64), to obtain the title compound (2.03g, yield 60-90%).

1H NMR(400MHz, CDCl ₃ )51.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 2.07(br s, 1H), 2.74(br s, 1H), 3.71~3.76(m, 1H), 4.87(d, J=4.8Hz, 1H), 6.99~7.52(m, 4H)

Preparation Example 90: Synthesis of l-(3-iodophenyl)-(R,R)-l,2-butanediol

The substantially same method as described in Preparation Example 84 was conducted, except that l-(3-iodophenyl)-trans-l-butene (Preparation Example 76) was used instead of l-(2- iodophenyl)-trans-l-propene (Preparation Example 64), to obtain the title compound (1.18g, yield 60-90%).

1H NMR(400MHz, CDCl ₃ )51.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 2.07(br s, 1H), 2.74(br s, 1H), 3.71~3.76(m, 1H), 4.87(d, J=4.8Hz, 1H), 6.99~7.52(m, 4H)

Preparation Example 91: Synthesis of l-(3-iodophenyl)-3-methyl-(S,S)-l,2- butanediol The substantially same method as described in Preparation Example 83 was conducted, except that 1 -(3 -iodophenyl)-3 -methyl-trans- l-butene(Preparation Example 77) was used instead of l-(2-iodophenyl)-3 -methyl-trans- l-butene(Preparation Example 70), to obtain the title compound (0.5 lg, yield 60-90%).

1H NMR(400MHz, CDC1 ₃ ) 51.07(t, J=7.2Hz, 6H), 1.83~1.89(m, 1H), 1.92(d, J=5.6Hz, 1H), 2.69(d, J=6.4Hz, 1H), 3.53~3.56(m, 1H), 5.22~5.25(m, 1H), 6.92~7.50(m, 4H)

Preparation Example 92: Synthesis of l-(3-iodophenyl)-3-methyl-(R,R)-l,2- butanediol

The substantially same method as described in Preparation Example 90 was conducted, except that 1 -(3 -iodophenyl)-3 -methyl-trans- l-butene(Preparation Example 77) was used instead of l-(3-iodophenyl)-trans-l-butene (Preparation Example 76), to obtain the title compound (1.1 Og, yield 60-90%).

1H NMR(400MHz, CDC1 ₃ ) 61.07(t, J=7.2Hz, 6H), 1.83~1.89(m, 1H), 1.92(d, J=5.6Hz, 1H), 2.69(d, J=6.4Hz, 1H), 3.53~3.56(m, 1H), 5.22~5.25(m, 1H), 6.92~7.50(m, 4H)

Preparation Example 93: Synthesis of l-(3-iodophenyl)-(S,S)-l,2-hexanediol

The substantially same method as described in Preparation Example 85 was conducted, except that l-(3-iodophenyl)-trans-l-hexene(Preparation Example 78) was used instead of l-(2- iodophenyl)-trans-l-hexene(Preparation Example 71), to obtain the title compound (0.95g, yield 60-90%)

1H NMR(400MHz, CDC1 ₃ ) 60.90(t, J=7.2Hz, 3H), 1.35-1.65(m, 6H), 2.08(d, J=4.4Hz, 1H), 2.71(d, J=5.2Hz, 1H), 3.78-3.83(m, 1H), 5.04(t, J=5.0Hz, 1H), 6.95~7.49(m, 4H)

Preparation Example 94: Synthesis of l-(3-iodophenyl)-(R,R)-l,2-hexanediol

The substantially same method as described in Preparation Example 86 was conducted, except that l-(3-iodophenyl)-trans-l-hexene(Preparation Example 78) was used instead of l-(2- iodophenyl)-trans-l-hexene(Preparation Example 71), to obtain the title compound (0.4 lg, yield 60-90%)

1H NMR(400MHz, CDC1 ₃ ) 60.90(t, J=7.2Hz, 3H), 1.35~1.65(m, 6H), 2.08(d, J=4.4Hz, 1H), 2.71(d, J=5.2Hz, 1H), 3.78~3.83(m, 1H), 5.04(t, J=5.0Hz, 1H), 6.95~7.49(m, 4H)

Preparation Example 95: Synthesis of l-(4-fluorophenyi)-(S,S)-l,2-propanediol

The substantially same method as described in Preparation Example 87 was conducted, except that l-(4-fluorophenyl)-trans-l-propene (Preparation Example 79) was used instead of 1- (3-iodophenyl)-trans-l-propene (Preparation Example 75), to obtain the title compound (2.01g, yield 60-90%).

1H NMR(400MHz, CDC1 ₃ ) 51.15(d, J=6.4Hz, 3H), 2.43(d, J=3.6Hz, 1H), 2.69(d, J=4.8Hz, 1H), 3.90~3.98(m, 1H), 4.78(dd, J=4.4, 7.2Hz, 1H), 6.85~7.04(m, 4H)

Preparation Example 96: Synthesis of l-(3-fluorophenyl)-(R,R)-1.2-propanediol

The substantially same method as described in Preparation Example 88 was conducted, except that l-(4-fluorophenyl)-trans-l-propene (Preparation Example 79) was used instead of 1- (3-iodophenyl)-trans-l-propene (Preparation Example 75), to obtain the title compound (1.27g, yield 60-90%).

1H NMR(400MHz, CDC1 ₃ ) 51.15(d, J=6.4Hz, 3H), 2.43(d, J=3.6Hz, 1H), 2.69(d, J=4.8Hz, 1H), 3.90~3.98(m, 1H), 4.78(dd, J=4.4, 7.2Hz, 1H), 6.85~7.04(m, 4H) Preparation Example 97: Synthesis of l-(4-fluorophenyl)-(S,S)-l,2-butanediol

The substantially same method as described in Preparation Example 89 was conducted, except that l-(4-fluorophenyl)-trans-l-butene (Preparation Example 80) was used instead of 1- (3-iodophenyl)-trans-l-butene (Preparation Example 76), to obtain the title compound (0.43 g, yield 60-90%).

1H NMR(400MHz, CDCl ₃ )61.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 2.07(br s, 1H), 2.74(br s, 1H), 3.71~3.76(m, 1H), 4.87(d, J=4.8Hz, 1H), 6.88~7.05(m, 4H)

Preparation Example 98: Synthesis of l-(3-fluorophenyl)-(R,R)-l,2-butanediol

The substantially same method as described in Preparation Example 90 was conducted, except that l-(4-fluorophenyl)-trans-l-butene (Preparation Example 80) was used instead of 1- (3-iodophenyl)-trans-l-butene (Preparation Example 76), to obtain the title compound (1.13g, yield 60-90%).

1H NMR(400MHz, CDCl ₃ )61.04(t, J=7.6Hz, 3H), 1.60-1.7 l(m, 2H), 2.07(br s, 1H), 2.74(br s, 1H), 3.71~3.76(m, 1H), 4.87(d, J=4.8Hz, 1H), 6.88~7.05(m, 4H)

Preparation Example 99: Synthesis of l-(4-fiuorophenyl)-3-methyl-(S,S)-l,2- butanediol

The substantially same method as described in Preparation Example 91 was conducted, except that l-(4-fluorophenyl)-3 -methyl-trans- l-butene(Preparation Example 81) was used instead of 1 -(3 -iodophenyl)-3 -methyl -trans- l-butene(Preparation Example 77), to obtain the title compound (0.7 lg, yield 60-90%). 1H NMR(400MHz, CDC1 ₃ ) 51.07(t, J=7.2Hz, 6H), 1.83~1.89(m, 1H), 1.92(d, J=5.6Hz, 1H), 2.69(d, J=6.4Hz, 1H), 3.53~3.56(m, 1H), 5.22~5.25(m, 1H), 6.87~7.02(m, 4H)

Preparation Example 100: Synthesis of l-(3-fluorophenyl)-3-methyl-(R,R)-l,2- butanediol

The substantially same method as described in Preparation Example 92 was conducted, except that 1 -(4- fluorophenyl)-3 -methyl -trans- l-butene(Preparation Example 81) was used instead of 1 -(3 -iodophenyl)-3 -methyl -trans- 1 -butene(Preparation Example 77), to obtain the title compound (1.21g, yield 60-90%).

1H NMR(400MHz, CDC1 ₃ ) 61.07(t, J=7.2Hz, 6H), 1.83~1.89(m, 1H), 1.92(d, J=5.6Hz, 1H), 2.69(d, J=6.4Hz, 1H), 3.53~3.56(m, 1H), 5.22~5.25(m, 1H), 6.87~7.02(m, 4H)

Preparation Example 101: Synthesis of l-(4-fluorophenyl)-(S,S)-l,2-hexanediol

The substantially same method as described in Preparation Example 93 was conducted, except that l-(4-fluorophenyl)-trans-l-hexene(Preparation Example 82) was used instead of 1- (3-iodophenyl)-trans-l-hexene(Preparation Example 78), to obtain the title compound (1.13g, yield 60-90%)

1H NMR(400MHz, CDC1 ₃ ) 50.90(t, J=7.2Hz, 3H), 1.35-1.65(m, 6H), 2.08(d, J=4.4Hz, 1H), 2.71(d, J=5.2Hz, 1H), 3.78~3.83(m, 1H), 5.04(t, J=5.0Hz, 1H), 6.88~7.09(m, 4H)

Preparation Example 102: Synthesis of l-(3-fluorophenyl)-(R,R)-l,2-hexanediol

The substantially same method as described in Preparation Example 94 was conducted, except that l-(4-fluorophenyl)-trans-l-hexene(Preparation Example 82) was used instead of 1- (3-iodophenyl)-trans-l-hexene(Preparation Example 78), to obtain the title compound (1.42g, yield 60-90%)

1H NMR(400MHz, CDC1 ₃ ) 50.90(t, J=7.2Hz, 3H), 1.35~1.65(m, 6H), 2.08(d, J=4.4Hz, 1H), 2.71(d, J=5.2Hz, 1H), 3.78~3.83(m, 1H), 5.04(t, J=5.0Hz, 1H), 6.88~7.09(m, 4H)

Preparation Example 103: Synthesis of l-(2-chlorophenyl)-(S)-l-hydroxypropyI- (S)-2-carbamate

l-(2-chlorophenyl)-(S,S)-l,2-propanediol(2.33g) obtained in Preparation Example 14, tetrahydrofuran (THF, 12ml), and carbonyldiimidazole (CDI, 3.04g) were put into a flask and stirred at the room temperature. After approximately 3 hours, ammonia solution (NH ₄ OH, 4ml) was added thereto. When the reaction was completed, the obtained product was washed with 1M HC1 solution and ethylacetate (EA). The separated organic layer was dehydrated with anhydrous magnesium sulfate (MgS0 ₄ ), filtrated, and concented under reduced pressure. The concentrated residue was purified by a silica gel column chromatography, to obtain the title compound (1.40g, yield 49%).

M.P. 83-84 ^° C

1H NMR(400MHz, CDC1 ₃ ) 51.24(d, J=6.4Hz, 3H), 2.91(d, J=4.8Hz, 1H), 4.68(br s, 2H), 5.06~5.09(m, 1H), 5.18~5.21(m, 1H), 7.23~7.55(m, 4H)

¹³ C NMR(100MHz, CDC1 ₃ ) 516.4, 73.1, 75.0, 127.0, 128.4, 129.1, 129.5, 132.7, 138.0,

156.6

Preparation Example 104: Synthesis of l-(2-chlorophenyl)-(R)-l-hydroxypropyl- (R)-2-carbamate

The substantially same method as described in Preparation Example 10303 was conducted, except that l-(2-chlorophenyl)-(R,R)-l,2-propanediol obtained in Preparation Example 15 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (1.74g, yield 50%).

M.P. 85-86 ^° C

Ή NMR(400MHz, CDC1 ₃ ) 51.24(d, J=6.4Hz, 3H), 2.98(d, J=4.0Hz, 1H), 4.73(br s, 2H), 5.04~5.10(m, 1H), 5.18~5.20(m, 1H), 7.24~7.55(m, 4H)

Preparation Example 105: Synthesis of l-(2-chlorophenyl)-l-hydroxypropyl-2- carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that the mixture of l-(2-chlorophenyl)-(S,S)-l,2-propanediol and l-(2-chlorophenyl)- (R,R)-l,2-propanediol obtained in Preparation Example 16 was used instead of l-(2- chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.4 lg, yield 38%).

1H NMR(400MHz, CDC1 ₃ ) 51.14(d, J = 6.8Hz, 3H), 3.34(d, J = 3.2Hz, 1H), 5.06(brs, 2H), 5.09~5.15(m, 1H), 5.31(br t, J= 2.4Hz, 1H), 7.18~7.59(m, 4H)

Preparation Example 106: Synthesis of l-(2-chlorophenyl)-(R)-l-hydroxypropyl- (S)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2-chlorophenyl)-(R,S)-l,2-propanediol obtained in Preparation Example 55 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (1.7g, yield 50%).

1H NMR(400MHz, CDC13) 51.20(d, J=6.8, 3H), 2.68(s, 1H), 4.67(s, 2H), 5.16~5.22(m, 1H), 5.36(t, J=3.2, 1H), 7.23~7.61(m, 4H) Preparation Example 107: Synthesis of l-(2-chlorophenyl)-(S)-l-hydroxypropyl-

(R)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2-chlorophenyl)-(S,R)-l,2-propanediol obtained in Preparation Example 56 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (1.74g, yield 50%).

1H NMR(400MHz, CDC13) 61.20(d, J=6.4, 3H), 2.83(d, J=3.6, 1H), 4.78(s, 2H), 5.15~5.21(m, 1H), 5.36(t, J=3.2, 1H), 7.23~7.63(m, 4H)

Preparation Example 108 : Synthesis of l-(2-chlorophenyl)-(S)-l-hydroxybutyl-(S)- 2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2-chlorophenyl)-(S,S)-l,2-butanediol . obtained in Preparation Example 17 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (l.Og, yield 45%).

1H NMR(400MHz, CDC1 ₃ ) 50.96(t, J = 7.4Hz, 3H), 1.57~1.73(m, 2H), 3.01(d, J = 5.6Hz, 1H), 4.74(br s, 2H), 4.95(dt, J = 7.2, 8.8Hz, 1H), 5.23(t, J = 5.6Hz, 1H), 7.22~7.54(m, 4H)

Preparation Example 109 : Synthesis of l-(2-chlorophenyl)-(R)-l-hydroxybtyl-(R)- 2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2-chlorophenyl)-(R,R)-l,2-butanediol obtained in Preparation Example 18 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (1.5g, yield 25%).

1H NMPv(400MHz, CDC1 ₃ ) δ 0.94(t, J=7.4Hz, 3H), 1.53~1.73(m, 2H), 2.92(s, 1H), 4.78(br s, 2H), 4.91~4.96(m, 1H), 5.22(d, J=5.5Hz, 1H), 7.20~7.54(m, 4H)

Preparation Example 110 : Synthesis of l-(2-chlorophenyI)-l-hydroxybutyl-2- carbamate(8)

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2-chlorophenyl)-l,2-butanediol obtained in Preparation Example 19 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (1.8g, yield

30%).

Ή NMR(400MHz, CDC1 ₃ ) δ 0.97(t, J=7Hz, 3H), 1.58~1.74(m, 2H), 2.94(d, J=6Hz, 1H), 4.69(br s, 2H), 4.94~4.99(m, 1H), 5.24(t, J=6Hz, 1H), 7.23~7.56(m, 4H)

Preparation Example 111: Synthesis of l-(2-chlorophenyl)-(S)-l-hydroxy-3-methyl- butyl-(S)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2-chlorophenyl)-3-methyl-(S,S)-l,2-butanediol obtained in Preparation Example 20 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.72g, yield 48%).

1H NMR(400MHz, CDC1 ₃ ) 51.01(d, J = 6.4Hz, 3H), 1.09(d, J = 6.8Hz, 3H), 2.06(m, 1H), 2.75(d, J = 6.8Hz, 1H), 4.58(br s, 2H), 4.85~4.88(m, 1H), 5.34~5.37(m, 1H), 7.22~7.33(m, 2H), 7.35~7.37(m, 1H), 7.51~7.53(m, 1H) Preparation Example 112: Synthesis of l-(2-chlorophenyl)-(R)-l-hydroxy-3- methyl-butyl-(R)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2-chlorophenyl)-3-methyl-(R,R)- 1,2-butanediol obtained in Preparation Example 21 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.56g, yield 43%).

1H NMR(400MHz, CDC1 ₃ ) 51.01(d, J = 6.8Hz, 3H), 1.09(d, J = 6.8Hz, 3H), 2.06(m, 1H), 2.73(d, J = 6.8Hz, 1H), 4.57(br s, 2H), 4.85~4.88(m, 1H), 5.34~5.37(m, 1H), 7.24~7.30(m, 2H), 7.35~7.37(m, 1H), 7.51~7.53(m, 1H)

Preparation Example 113 : Synthesis of l-(2-chlorophenyl)-l-hydroxy-3-methyl- butyl-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2-chlorophenyl)-3 -methyl- 1,2-butanediol obtained in Preparation Example 22 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (1.5g, yield 23%).

1H NMR(400MHz, CDC1 ₃ ) 61.00(d, J=6.4Hz, 3H), 1.09(d, J=6.4Hz, 3H), 2.08(m, 1H), 2.76(d, J=6.0Hz, 1H), 4.59(br s, 2H), 4.87(dd, J=7.2Hz, 4.4Hz, 1H), 5.36(t, J=4.6, 1H), 7.23~7.54(m, 4H)

Preparation Example 114: Synthesis of l-(2-chlorophenyl)-(S)-l-hydroxyhexyl-(S)- 2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2-chlorophenyl)-(S,S)-l,2-hexanediol obtained in Preparation Example 23 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.24g, yield 49%).

1H NMR(400MHz, CDC1 ₃ ) 50.88(t, J= 7Hz, 3H), 1.33~1.42(m, 4H), 1.53~1.71(m, 2H), 2.89(d, J = 5.6Hz, 1H) 4.64(br s, 2H), 5.04(dt, J = 5.0, 9.0Hz, 1H), 5.20(t, J = 5.6Hz, 1H), 7.23~7.55(m, 4H)

Preparation Example 115: Synthesis of l-(2-chlorophenyI)-(R)-l-hydroxyhexyl-(R)- 2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2-chlorophenyl)-(R,R)-l,2-hexanediol obtained in Preparation Example 24 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (2.2g, yield 44%).

l NMR(400MHz, CDC1 ₃ ) δ 0.89(dd, J=5Hz, 3H), 1.28~1.43(m, 4H), 1.52~1.58(m, 1H), 1.65~1.72(m, 1H), 2.90(d, J=6Hz, 1H), 4.64(br s, 2H), 5.01~5.06(m, 1H), 5.22(t, J=6Hz, 1H), 7.22~7.56(m, 4H)

Preparation Example 116: Synthesis of l-(2-chlorophenyl)-l-hydroxyhexyl-2- carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2-chlorophenyl)-l,2-hexanediol obtained in Preparation Example 25 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (1.6g, yield 34%).

Ή NMR(400MHz, CDC1 ₃ ) δ 0.88(dd, J=5Hz, 3H), 1.31~1.43(m, 4H), 1.63~1.70(m, 1H), 1.52~1.60(m, 1H), 3.06(d, J=6Hz, 1H), 4.75(br s, 2H), 5.00~5.05(m, 1H), 5.21(t, J=6Hz, 1H), 7.22~7.55(m, 4H)

Preparation Example 117: Synthesis of l-(2-chlorophenyl)-(S)-l-hydroxypropyl- (S)-2-meth lcarbamate

The substantially same method as described in Preparation Example 103 was conducted, except that methylamine was used instead of ammonia solution(NH OH), to obtain the title compound (1.6g, yield 51%).

1H NMR(400MHz, CDC1 ₃ ) 51.03~1.25(m, 3H), 2.76(s, 3H), 3.34(s, 1H), 4.80(br s 1H), 5.04(t, J=12.5Hz, 1H), 5.14(s, 1H), 7.20~7.53(m, 4H)

Preparation Example 118: Synthesis of l-(2-chlorophenyl)-(S)-l-hydroxypropyl- (S)-2-propylcarbamate

The substantially same method as described in Preparation Example 103 was conducted, except that propylamine was used instead of ammonia solution(NH ₄ OH), to obtain the title compound (0.79g, yield 25%).

Ή NMR(400MHz, CDC1 ₃ ) 60.90(t, J=6.8Hz, 3H), 1.20(d, J=5.96Hz, 3H), 1.49(dd, J=14.2Hz, 2H), 3.11(d, J=6.28Hz, 2H), 3.34(s, 1H), 4.84(br s, 1H), 5.05(t, J=5.88Hz, 1H), 5.14(s, 1H), 7.22~7.53(m, 4H) Preparation Example 119: Synthesis of l-(2-chIorophenyl)-(S)-l-hydroxypropyl- (R)-2-isopropyIcarbamate

The substantially same method as described in Preparation Example 103 was conducted, except that isopropylamine was used instead of ammonia solution( H ₄ OH), to obtain the title compound (1.5g, yield 41%).

1H NMR(400MHz, CDC1 ₃ ) 61.14(dd, J=6.5Hz, 6H), 1.19(d, J=6.4Hz, 3H), 3.21(s, 1H), 3.73~3.82(m, 1H), 4.59(br s, 1H), 5.01~5.07(m, 1H), 5.14(t, J=5.8Hz, 1H), 7.20~7.53(m, 4H)

Preparation Example 120: Synthesis of l-(2-chlorophenyl)-(S)-l-hydroxypropyl- (R)-2-cyclopropylcarbamate

The substantially same method as described in Preparation Example 103 was conducted, except that cyclopropylamine was used instead of ammonia solution(NH ₄ OH), to obtain the title compound (2.2g, yield 43%).

1H NMR(400MHz, CDC1 ₃ ) 50.50~0.56(m, 2H), 0.74(d, J=7.21Hz, 2H), 1.25(s, 3H), 2.56~2.61(m, 1H), 3.72(s, 1H), 4.98(br s, 1H), 5.05-5. l l(m, 1H), 7.16(s, 1H), 7.23~7.54(m, 4H)

Preparation Example 121: Synthesis of l-(2-chlorophenyl)-(S)-l-hydroxypropyl- (R)-2-c clohexyl carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that cyclohexylamine was used instead of ammonia solution(NH ₄ 0H), to obtain the title compound (l .lg, yield 26%). 1H NMR(400MHz, CDC1 ₃ ) 51.06~1.40(m, 7H), 1.56~1.61(m, 2H), 1.69~1.71(m, 2H), 1.87~1.94(m, 2H), 3.19(d, J=4.32Hz, 1H), 3.45(s, 1H), 4.64(br s 1H), 5.02~5.07(m, 1H), 5.14(t, J=6.08Hz, 1H) 7.20~7.53(m, 4H)

Preparation Example 122: Synthesis of l-(2-chlorophenyl)-(S)-l-hydroxypropyl- (S)-2-benzyl carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that benzylamine was used instead of ammonia solution(NH ₄ OH), to obtain the title compound (1.2g, yield 18%).

1H NMR(400MHz, CDC1 ₃ ) δ 1.27(d, J=10Hz, 3H), 3.12(d, J=5Hz, 1H), 4.37(d, J=6Hz, 2H), 5.12~5.19(m, 3H), 7.15~7.56(m, 9H)

Preparation Example 123: Synthesis of l-(2-chlorophenyl)-(S)-l-hydroxypropyl- (S)-2-bic clo[2,2,l]heptanescarbamate

The substantially same method as described in Preparation Example 103 was conducted, except that 2-aminonorbornane was used instead of ammonia solution(NH ₄ OH), to obtain the title compound (1.7g, yield 32%).

1H NMR(400MHz, CDC1 ₃ ) 61.08~1.35(m, 9H), 1.65(br s, 1H), 1.75~1.71(m, 1H), 2.14~2.24(m, 1H), 2.27~2.30(m, 1H), 3.23~3.29(m, 1H), 3.47~3.52(m, 1H), 4.67(br s, 1H), 5.01~5.09(m, 1H), 5.12-5.18(m, 1H), 7.22~7.55(m, 4H)

Preparation Example 124: Synthesis of l-(2-chlorophenyl)-(R)-l-hydroxypropyl- (R)-2-methylcarbamate

The substantially same method as described in Example 2 was conducted, except that methylamine was used instead of ammonia solution(NH ₄ OH), to obtain the title compound (3.36g, yield 60%).

1H NMR(400MHz, CDC1 ₃ ) δ 1.20(d, J=6.8Hz, 3H), 2.80(d, J=4.8Hz, 3H), 3.20(d, J=4.4Hz, 1H), 4.75(br s, 1H), 5.03~5.09(m, 1H), 5.14~5.17(m, 1H), 7.22~7.55(m, 4H)

Preparation Example 125: Synthesis of l-(2-chlorophenyl)-(R)-l-hydroxypropyl- (R)-2-pro lcarbamate

The substantially same method as described in Preparation Example 104 was conducted, except that propylamine was used instead of ammonia solution(NH ₄ OH), to obtain the title compound (3.1 g, yield 53 %) .

1H NMR(400MHz, CDC1 ₃ ) 50.92(t, J=7.6Hz, 3H), 1.21(d, J=6.4Hz, 3H), 1.51(m, 2H), 3.09-3.14(m, 2H), 3.28(d, J=4.4Hz, 1H), 4.82(br s, 1H), 5.03~5.09(m, 1H), 5.14~5.17(m, 1H), 7.22~7.55(m. 4H)

Preparation Example 126: Synthesis of l-(2-chlorophenyl)-(R)-l-hydroxypropyl- (R)-2-iso ropylcarbamate

The substantially same method as described in Preparation Example 104 was conducted, except that isopropylamine was used instead of ammonia solution(NH ₄ OH), to obtain the title compound (0.16g, yield 27%).

1H NMR(400MHz, CDC1 ₃ ) 60.88~1.16(m, 6H), 1.19~1.26(m, 3H), 3.34(s, 1H), 3.71~3.78(m, 1H), 4.62(br s, 1H), 5.03(t, J=5.8Hz, 1H), 5.13(d, J=4.9Hz, 1H), 7.20~7.53(m, 4H)

Preparation Example 127: Synthesis of l-(2-chlorophenyl)-(R)-l-hydroxypropyl- (R)-2-cyclopropylcarbamate

The substantially same method as described in Preparation Example 104 was conducted, except that cyclopropylamine was used instead of ammonia solution( H ₄ 0H), to obtain the title compound (3.7g, yield 60%).

Ή NMR(400MHz, CDC1 ₃ ) 50.49~0.54(m, 2H), 0.74(d, J=7.2Hz, 2H), 1.22(s, 3H), 2.55~2.60(m, 1H), 3.16(s, 1H), 5.00(s, 1H), 5.04~5.11(m, 1H), 5.16(s, 1H), 7.23~7.54(m, 4H)

Preparation Example 128: Synthesis of l-(2-chlorophenyl)-(R)-l-hydroxypropyl- (R)-2-cyclohexyl carbamate

The substantially same method as described in Preparation Example 104 was conducted, except that cyclohexylamine was used instead of ammonia solution(NH ₄ OH), to obtain the title compound (1.9g, yield 28%).

1H NMR(400MHz, CDC1 ₃ ) 51.05~1.38(m, 8H), 1.58~1.70(m, 3H), 1.85~1.95(m, 2H), 3.39~3.47(m, 1H), 3.56(s, 1H), 4.79(br s, 1H), 5.01~5.07(m, 1H), 5.14(t, J=5.2Hz, 1H), 7.20~7.54(m, 4H)

Preparation Example 129: Synthesis of l-(2-chlorophenyl)-(R)-l-hydroxypropyl- (R)-2-benzylcarbamate

The substantially same method as described in Preparation Example 104 was conducted, except that benzylamine was used instead of ammonia solution(NH ₄ OH), to obtain the title compound (0.52g, yield 19%).

1H NMR(400MHz, CDC1 ₃ ) 81.25(d, J=6Hz, 3H), 1.64(s, 1H), 3.13(d, J=4.4Hz, 1H), 4.37(d, J=5.6Hz, 2H), 5.12~5.19(m, 2H), 7.23~7.55(m, 9H)

Preparation Example 130: Synthesis of l-(2-chlorophenyl)-(R)-l-hydroxypropyl- (R)-2-bicyclo[2,2,l]heptanecarbamate

The substantially same method as described in Preparation Example 104 was conducted, except that 2-aminonorbornane was used instead of ammonia solution(NH ₄ OH), to obtain the title compound (1.7g, yield 20-50%).

1H NMR(400MHz, CDC1 ₃ ) 51.08~1.35(m, 9H), 1.65(br s, 1H), 1.75~1.71(m, 1H), 2.14~2.24(m, 1H), 2.27~2.30(m, 1H), 3.23~3.29(m, 1H), 3.47~3.52(m, 1H), 4.67(br s, 1H), 5.01~5.09(m, 1H), 5.12~5.18(m, 1H), 7.22~7.55(m, 4H)

Preparation Example 131: Synthesis of l-(2-chlorophenyl)-l-hydroxypropyl-2- methylcarbamate

The substantially same method as described in Preparation Example 105 was conducted, except that methylamine was used instead of ammonia solution(NH ₄ OH), to obtain the title compound (2.6g, yield 45%).

1H NMR(400MHz, CDC1 ₃ ) δ 1.21(d, J=6Hz, 3H), 2.81(d, J=5Hz, 3H), 3.14(d, J=4Hz, IH), 4.72(br s, IH), 5.07(dd, J=6Hz, IH), 5.16(t, J=6Hz, IH), 7.22~7.56(m, 4H)

Preparation Example 132: Synthesis of l-(2-chlorophenyI)-l-hydroxypropyl-2- propylcarbamate

The substantially same method as described in Preparation Example 105 was conducted, except that propylamine was used instead of ammonia solution(NH ₄ OH), to obtain the title compound (l .Og, yield 17%).

1H NMR(400MHz, CDC1 ₃ ) δ 0.92(t, J=7Hz, 3H), 1.21(d, J=6Hz, 3H), 1.53(dd, J=7Hz, 2H), 3.13(dd, J=7Hz, 2H), 3.28(d, IH), 4.82(S, IH), 5.06(dd, J=7Hz, IH), 5.16(t, J=5Hz, IH), 7.21~7.56(m, 4H)

Preparation Example 133: Synthesis of l-(2-chlorophenyl)-l-hydroxypropyl-2- isopropylcarbamate

The substantially same method as described in Preparation Example 105 was conducted, except that isopropylamine was used instead of ammonia solution(NH ₄ OH), to obtain the title compound (0.54g, yield 16%).

1H NMR(400MHz, CDC1 ₃ ) δ 1.16(dd, J=6Hz, 6H), 1.21(d, J=6Hz, 3H), 3.23(d, J=6Hz, IH), 3.75~3.84(m, IH), 4.61(br s, IH), 5.06(t, J=6Hz, IH), 5.16(t, J=6Hz, IH), 7.22~7.56(m, 4H)

Preparation Example 134: Synthesis of l-(2-chlorophenyl)-l-hydroxypropyl-2- cyclopropylcarbamate

The substantially same method as described in Preparation Example 105 was conducted, except that cyclopropylamine was used instead of ammonia solution(NH ₄ 0H), to obtain the title compound (l.Og, yield 17%).

1H NMR(400MHz, CDC1 ₃ ) δ 0.50(t, J=6Hz, 2H), 0.77(t, J=3Hz, 2H), 1.12(d, J=7Hz, 3H), 2.53~2.59(m, 1H), 3.22(d, J=4Hz, 1H), 5.08(dd, J=6Hz, 1H), 5.15(S, 1H), 7.22~7.55(m, 4H)

Preparation Example 135: Synthesis of l-(2-chlorophenyl)-l-hydroxypropyl-2- cyclohexylcarbamate

The substantially same method as described in Preparation Example 105 was conducted, except that cyclohexylamine was used instead of ammonia solution(NH ₄ OH), to obtain the title compound (2.2g, yield 33%).

1H NMR(400MHz, CDC1 ₃ ) δ 1.07-1.17(m, 3H), 1.21(d, J=6Hz, 3H), 1.29~1.42(m, 3H), 1.72(dd, J=6Hz, 2H), 1.92(dd, J=6Hz, 2H), 3.26(d, J=4Hz, 1H), 3.46(t, J=4Hz, 1H), 4.68(d, J=6Hz, 1H), 5.07(dd, J=6Hz, 1H), 5.16(t, J=6Hz, 1H), 7.22~7.55(m, 4H)

Preparation Example 136: Synthesis of l-(2-chlorophenyI)-l-hydroxypropyl-2- benzylcarbamate

The substantially same method as described in Preparation Example 105 was conducted, except that benzylamine was used instead of ammonia solution(NH ₄ OH), to obtain the title compound (1.3g, yield 19%).

1H NMR(400MHz, CDC1 ₃ ) 5 1.25(d, J=6Hz, 3H), 3.16(d, J=4Hz, 1H), 4.36(d, J=6Hz, 2H), 5.14(dd, J=6Hz, 3H), 7.23~7.56(m, 9H), yield: 19%(1.3g)

Preparation Example 137: Synthesis of l-(2-chlorophenyl)-l-hydroxypropyl-2- bicyclo [2,2,1] heptanecarbamate

The substantially same method as described in Preparation Example 105 was conducted, except that 2-aminonorbornane was used instead of ammonia solution(NH ₄ OH), to obtain the title compound (1.7g, yield 20-50%).

1H NMR(400MHz, CDC1 ₃ ) 51.08~1.35(m, 9H), 1.65(br s, 1H), 1.75~1.71(m, 1H), 2.14~2.24(m, 1H), 2.27~2.30(m, 1H), 3.23~3.29(m, 1H), 3.47~3.52(m, 1H), 4.67(br s, 1H), 5.01~5.09(m, 1H), 5.12~5.18(m, 1H), 7.22~7.55(m, 4H)

Preparation Example 138: Synthesis of l-(2,4-dich!orophenyl)-(S)-l- hydroxypropyl-(S)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,4-dichlorophenyl)-(S,S)-l,2-propanediol obtained in Preparation Example 26 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.14g, yield 34%).

1H NMR(400MHz, CDC1 ₃ ) 61.22(d, J= 6.4Hz, 3H), 4.16(br t, 1H) 4.96(br t, 3H), 5.07(t, J= 4.8Hz, 1H), 7.23~7.52(m, 3H)

Preparation Example 139 : Synthesis of l-(2,6-dichlorophenyl)-(S)-l- hydroxypropyl-(S)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,6-dichlorophenyl)-(S,S)-l,2-propanediol obtained in Preparation Example 38 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.22g, yield 49%).

Ή NMR(400MHz, CDC1 ₃ ) 51.15(d, J = 6.4Hz, 3H), 3.66(d, J = 9.2Hz, 1H), 4.73(br s, 2H), 5.43(t, J= 9.0Hz, 1H), 5.62~5.69(m, 1H), 7.18~7.22(m, 3H),

Preparation Example 140 : Synthesis of l-(2,3-dichlorophenyl)-(S)-l- hydroxypropyl-(S)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,3-dichlorophenyl)-(S,S)-l,2-propanediol obtained in Preparation Example 57 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.2 lg, yield 20-60%).

Ή NMR(400MHz, CDC1 ₃ ) 61.15(d, J = 6.4Hz, 3H), 3.66(d, J = 9.2Hz, 1H), 4.73(br s, 2H), 5.43(t, J= 9.0Hz, 1H), 5.62~5.69(m, 1H), 7.18~7.22(m, 3H),

Preparation Example 141: Synthesis of l-(2,4-dichlorophenyi)-(S)-l-hydroxybutyl- (S)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,4-dichlorophenyl)-(S,S)-l,2-butanediol obtained in Preparation Example 29 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.23g, yield 52%).

Ή NMR(400MHz, CDC1 ₃ ) 50.96(t, J = 7.4Hz, 3H), 1.58~1.74(m, 2H), 2.98(d, J = 5.6Hz, 1H) 4.68(br s, 2H), 5.59(dt, J= 5.2, 8.8Hz, 1H), 5.19(t, J= 5.4Hz, 1H), 7.30~7.50(m, 3H)

Preparation Example 142: Synthesis of l-(2,6-dichlorophenyl)-(S)-l-hydroxybutyl- (S)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,6-dichlorophenyl)-(S,S)-l,2-butanediol obtained in Preparation Example 41 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.49g, yield 34%).

1H NMR(400MHz, CDC1 ₃ ) 60.92(t, J = 7.4Hz, 3H), 1.30~1.38(m, 1H), 1.57~1.64(m, 1H), 3.74(d, J= 9.2Hz, 1H), 4.80(br s, 2H), 5.40~5.50(m, 2H), 7.17~7.34(m, 3H)

Preparation Example 143: Synthesis of l-(2,4-dichlorophenyI)-(S)-l-hydroxy-3- methyl-butyl-(S)-2-carb amate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,4-dichlorophenyl)-3-methyl-(S,S)-l,2-butanediol obtained in Preparation Example 32 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.13g, yield 20-60%).

1H NMR(400MHz, CDC1 ₃ ) 61.00(t, J = 7.2Hz, 6H), 1.73~1.79(m, 1H), 3.67~3.69(m, 1H), 4.85(br s, 2H), 5.40~5.43(m, 1H), 5.49~5.54(m, 1H), 7.30~7.50(m, 3H)

Preparation Example 144: Synthesis of l-(2,6-dichlorophenyl)-(S)-l-hydroxy-3- methyl-butyl-(S)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,6-dichlorophenyl)-3-methyl-(S,S)-l,2-butanediol obtained in Preparation Example 44 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.12g, yield 20%).

1H NMR(400MHz, CDC1 ₃ ) 61.00(t, J = 7.2Hz, 6H), 1.73~1.79(m, 1H), 3.67~3.69(m, 1H), 4.85(br s, 2H), 5.40~5.43(m, 1H), 5.49~5.54(m, 1H), 7.16~7.33(m, 3H)

Preparation Example 145: Synthesis of l-(2,4-dichlorophenyl)-(S)-l-hydroxyhexyl-

(S)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,4-dichlorophenyl)-(S,S)-l,2-hexanediol obtained in Preparation Example 35 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.94g, yield 81%).

1H NMR(400MHz, CDC1 ₃ ) δ0.89(ΐ, J = 3.6Hz, 3H), 1.28~1.42(m, 4H), 1.52~1.59(m, 1H), 1.64~1.71(m, 1H), 2.98(d, J = 5.6Hz, 1H), 4.67(br s, 2H), 4.96~5.00(m, 1H), 5.17(t, J = 5.6Hz, 1H), 7.30~7.49(m 3H)

Preparation Example 146: Synthesis of l-(2,6-dichlorophenyl)-(S)-l-hydroxyhexyl- (S)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,6-dichlorophenyl)-(S,S)-l,2-hexanediol obtained in Preparation Example 47 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.15g, yield 31%).

1H NMR(400MHz, CDC1 ₃ ) 50.84(t, J = 7.0Hz, 3H), 1.20~1.35(m, 4H), 1.36~1.41(m, 1H), 1.59~1.63(m, 1H), 3.71(d, J = 10.0Hz, 1H), 4.74(br s, 2H), 5.40~5.44(m, 1H), 5.52~5.57(m, 1H), 7.17~7.35(m, 3H) Preparation Example 147 : Synthesis of l-(2,4-dichlorophenyl)-(R)-l- hydroxypropyI-(R)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,4-dichlorophenyl)-(R,R)-l,2-propanediol obtained in Preparation Example 27 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.14g, yield 20-60%).

1H NMR(400MHz, CDC1 ₃ ) 51.22(d, J= 6.4Hz, 3H), 4.16(br t, 1H) 4.96(br t, 3H), 5.07(t, J= 4.8Hz, 1H), 7.23~7.52(m, 3H)

Preparation Example 148 : Synthesis of l-(2,6-dichlorophenyI)-(R)-l- hydroxypropyl-(R)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,6-dichlorophenyl)-(R,R)-l,2-propanediol obtained in Preparation Example 39 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.2 lg, yield 20-60%).

1H NMR(400MHz, CDC1 ₃ ) 51.15(d, J = 6.4Hz, 3H), 3.66(d, J = 9.2Hz, 1H), 4.73(br s, 2H), 5.43(t, J= 9.0Hz, 1H), 5.62~5.69(m, 1H), 7.18~7.22(m, 3H),

Preparation Example 149: Synthesis of l-(2,3-dichlorophenyl)-(R)-l- hydroxypropyl-(R)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,3-dichlorophenyl)-(R,R)-l,2-propanediol obtained in Preparation Example 58 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.08g, yield 20-60%).

Ή NMR(400MHz, CDC1 ₃ ) 51.15(d, J = 6.4Hz, 3H), 3.66(d, J = 9.2Hz, 1H), 4.73(br s, 2H), 5.43(t, J = 9.0Hz, 1H), 5.62~5.69(m, 1H), 7.18~7.22(m, 3H),

Preparation Example 150 : Synthesis of l-(2,4-dichlorophenyl)-(R)-l-hydroxybutyl- (R)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,4-dichlorophenyl)-(R,R)-l,2-butanediol obtained in Preparation Example 30 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.23g, yield 20-60%).

1H NMR(400MHz, CDC1 ₃ ) 50.96(t, J = 7.4Hz, 3H), 1.58~1.74(m, 2H), 2.98(d, J = 5.6Hz, 1H) 4.68(br s, 2H), 5.59(dt, J = 5.2, 8.8Hz, 1H), 5.19(t, J= 5.4Hz, 1H), 7.30~7.50(m, 3H)

Preparation Example 151 : Synthesis of l-(2,6-dich!orophenyl)-(R)-l-hydroxybutyl- (R)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,6-dichlorophenyl)-(R,R)-l,2-butanediol obtained in Preparation Example 42 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.49g, yield 20-60%).

1H NMR(400MHz, CDCI3) 60.92(t, J = 7.4Hz, 3H), 1.30~1.38(m, 1H), 1.57~1.64(m, 1H), 3.74(d, J= 9.2Hz, 1H), 4.80(br s, 2H), 5.40~5.50(m, 2H), 7.17~7.34(m, 3H) Preparation Example 152 : Synthesis of l-(2,4-dichlorophenyl)-(R)-l-hydroxy-3- methyl-butyl-(R)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,4-dichlorophenyl)-3-methyl-(R,R)-l,2-butanediol obtained in Preparation Example 33 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.23g, yield 20-60%).

1H NMPv(400MHz, CDC1 ₃ ) 61.00(t, J = 7.2Hz, 6H), 1.73~1.79(m, 1H), 3.67~3.69(m, 1H), 4.85(br s, 2H), 5.40~5.43(m, lH), 5.49~5.54(m, 1H), 7.30~7.50(m, 3H)

Preparation Example 153 : Synthesis of l-(2,6-dichlorophenyl)-(R)-l-hydroxy-3- methyl-butyl-(R)-2-carb amate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,6-dichlorophenyl)-3-methyl-(R,R)-l,2-butanediol obtained in Preparation Example 45 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.14g, yield 20-60%).

1H NMR(400MHz, CDC1 ₃ ) 61.00(t, J = 7.2Hz, 6H), 1.73~1.79(m, 1H), 3.67~3.69(m, 1H), 4.85(br s, 2H), 5.40~5.43(m, 1H), 5.49~5.54(m, 1H), 7.16~7.33(m, 3H)

Preparation Example 154: Synthesis of l-(2,4-dichlorophenyl)-(R)-l-hydroxyhexyl- (R)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,4-dichlorophenyl)-(R,R)-l,2-hexanediol obtained in Preparation Example 36 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.84g, yield 20-60%).

Ή NMR(400MHz, CDC1 ₃ ) 50.89(t, J = 3.6Hz, 3H), 1.28~1.42(m, 4H), 1.52~1.59(m, 1H), 1.64~1.71(m, 1H), 2.98(d, J = 5.6Hz, 1H), 4.67(br s, 2H), 4.96~5.00(m, 1H), 5.17(t, J = 5.6Hz, 1H), 7.30~7.49(m, 3H)

Preparation Example 155: Synthesis of l-(2,6-dichlorophenyl)-(R)-l-hydroxyhexyl- (R)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,6-dichlorophenyl)-(R,R)-l,2-hexanediol obtained in Preparation Example 48 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.15g, yield 20-60%).

1H NMR(400MHz, CDC1 ₃ ) 80.84(t, J = 7.0Hz, 3H), 1.20~1.35(m, 4H), 1.36~1.41(m, 1H), 1.59~1.63(m, 1H), 3.71 (d, J= 10.0Hz, 1H), 4.74(br s, 2H), 5.40~5.44(m, 1H), 5.52~5.57(m, 1H), 7.17-7.35(m, 3H)

Preparation Example 156 : Synthesis of l-(2,4-dichlorophenyl)-l-hydroxypropyl-2- carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,4-dichlorophenyl)-l,2-propanediol obtained in Preparation Example 28 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.14g, yield 20-60%).

1H NMR(400MHz, CDC1 ₃ ) 61.22(d, J= 6.4Hz, 3H), 4.16(br t, 1H) 4.96(br t, 3H), 5.07(t, J= 4.8Hz, 1H), 7.23~7.52(m, 3H)

Preparation Example 157 : Synthesis of l-(2,6-dichlorophenyI)-l-hydroxypropyl-2- carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,6-dichlorophenyl)-l,2-propanediol obtained in Preparation Example 40 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.19g, yield 20-60%).

1H NMR(400MHz, CDC1 ₃ ) 51.15(d, J = 6.4Hz, 3H), 3.66(d, J = 9.2Hz, 1H), 4.73(br s, 2H), 5.43(t, J= 9.0Hz, 1H), 5.62~5.69(m, 1H), 7.18~7.22(m, 3H)

Preparation Example 158 : Synthesis of l-(2,3-dichlorophenyl)-l-hydroxypropyl-2- carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,3-dichlorophenyl)-l,2-propanediol obtained in Preparation Example 59 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.21g, yield 20-60%).

1H NMR(400MHz, CDC1 ₃ ) 51.15(d, J = 6.4Hz, 3H), 3.66(d, J = 9.2Hz, 1H), 4.73(br s, 2H), 5.43(t, J= 9.0Hz, 1H), 5.62~5.69(m, 1H), 7.18-7.22(m, 3H),

Preparation Example 159: Synthesis of l-(2,4-dichlorophenyl)-l-hydroxybutyl-2- carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,4-dichlorophenyl)-l,2-butanediol obtained in Preparation Example 31 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.23g, yield 20-60%).

1H NMR(400MHz, CDC1 ₃ ) δ0.96(ΐ, J = 7.4Hz, 3H), 1.58~1.74(m, 2H), 2.98(d, J = 5.6Hz, 1H) 4.68(br s, 2H), 5.59(dt, J= 5.2, 8.8Hz, 1H), 5.19(t, J= 5.4Hz, 1H), 7.30~7.50(m, 3H)

Preparation Example 160: Synthesis of l-(2,6-dichlorophenyl)-l-hydroxybutyl-2- carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,6-dichlorophenyl)-l,2-butanediol obtained in Preparation Example 43 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.49g, yield 20-60%).

1H NMR(400MHz, CDC1 ₃ ) 60.92(t, J = 7.4Hz, 3H), 1.30~1.38(m, 1H), 1.57~1.64(m, 1H), 3.74(d, J= 9.2Hz, 1H), 4.80(br s, 2H), 5.40~5.50(m, 2H), 7.17~7.34(m, 3H)

Preparation Example 161: Synthesis of l-(2,4-dichlorophenyl)-l-hydroxy-3-methyl- butyl-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,4-dichlorophenyl)-3-methyl-l,2-butanediol obtained in Preparation Example 34 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.13g, yield 20-60%).

1H NMR(400MHz, CDC1 ₃ ) 51.00(t, J = 7.2Hz, 6H), 1.73~1.79(m, 1H), 3.67~3.69(m, 1H), 4.85(br s, 2H), 5.40~5.43(m, 1H), 5.49~5.54(m, 1H), 7.30~7.50(m, 3H)

Preparation Example 162: Synthesis of l-(2,6-dichlorophenyl)-l-hydroxy-3-methyl- butyl-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,6-dichlorophenyl)-3-methyl-l,2-butanediol obtained in Preparation Example 46 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.13g, yield 20-60%).

1H NMR(400MHz, CDC1 ₃ ) 61.00(t, J = 7.2Hz, 6H), 1.73~1.79(m, 1H), 3.67~3.69(m, 1H), 4.85(br s, 2H), 5.40~5.43(m, 1H), 5.49~5.54(m, 1H), 7.16~7.33(m, 3H)

Preparation Example 163 : Synthesis of l-(2,4-dichlorophenyI)-l-hydroxyhexyl-2- carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,4-dichlorophenyl)-l,2-hexanediol obtained in Preparation Example 37 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.94g, yield 20-60%).

1H NMR(400MHz, CDC1 ₃ ) 50.89(t, J = 3.6Hz, 3H), 1.28~1.42(m, 4H), 1.52~1.59(m, 1H), 1.64~1.71(m, 1H), 2.98(d, J = 5.6Hz, 1H), 4.67(br s, 2H), 4.96~5.00(m, 1H), 5.17(t, J = 5.6Hz, 1H), 7.30~7.49(m, 3H)

Preparation Example 164 : Synthesis of l-(2,6-dichlorophenyl)-l-hydroxyhexyl-2- carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,6-dichlorophenyl)-l,2-hexanediol obtained in Preparation Example 49 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (0.15g, yield 20-60%).

1H NMR(400MHz, CDC1 ₃ ) 50.84(t, J = 7.0Hz, 3H), 1.20~1.35(m, 4H), 1.36~1.41(m, 1H), 1.59~1.63(m, 1H), 3.71(d, J= 10.0Hz, 1H), 4.74(br s, 2H), 5.40~5.44(m, 1H), 5.52~5.57(m, 1H), 7.17-7.35(m, 3H)

Preparation Example 165 : Synthesis of l-(2-fluorophenyl)-(S)-l-hydroxypropyl- (S)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2-fluorophenyl)-(S,S)-l,2-propanediol(12.23g) obtained in Preparation Example 61 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (6.11g, yield 40%).

1H NMR(400MHz, CDC1 ₃ ) 51.19(d, J=5.2Hz, 3H), 2.93(d, J=4.4Hz, 1H), 4.71(br s, 2H), 4.99~5.06(m, H), 7.04~7.48(m, 4H)

Preparation Example 166 : Synthesis of l-(2-fluorophenyl)-(R)-l-hydroxypropyl- (R)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2-fluorophenyl)-(R,R)-l,2-propanediol(6.26g) obtained in Preparation Example 62 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (3.13g, yield 40%).

Ή NMR(400MHz, CDC1 ₃ ) 51.19(d, J=5.2Hz, 3H), 2.93(d, J=4.4Hz, 1H), 4.71(br s, 2H), 4.99~5.06(m, H), 7.04~7.48(m, 4H)

Preparation Example 167 : Synthesis of l-(2-iodophenyl)-(S)-l-hydroxypropyl-(S)- 2-carba

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2-iodophenyl)-(S,S)-l,2-propanediol obtained in Preparation Example 66 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (2.2g, yield 30-60%).

Ή NMR(400MHz, CDC1 ₃ ) 51.27(d, J=6.4Hz, 3H), 3.09(br s, 1H), 4.83(br s, 2H), 5.00-5.10(m, 2H), 7.00~7.76(m, 4H)

Preparation Example 168 : Synthesis of l-(2-iodophenyl)-(R)-l-hydroxypropyl-(R)- 2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2-iodophenyl)-(R,R)-l,2-propanediol obtained in Preparation Example 67 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (3.13g, yield 30-60%).

1H NMR(400MHz, CDC1 ₃ ) 61.27(d, J=6.4Hz, 3H), 2.95(d, J=3.6Hz, 1H), 4.73(br s, 2H), 5.01-5.1 l(m, 2H), 7.01~7.86(m, 4H)

Preparation Example 169 : Synthesis of l-(2-iodophenyl)-(S)-l-hydroxybutyl-(S)-2- carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2-iodophenyl)-(S,S)-l,2-butanediol obtained in Preparation Example 68 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (3.6g, yield 30-60%).

Ή NMR(400MHz, CDC1 ₃ ) 51.27(d, J=6.4Hz, 3H), 3.09(br s, 1H), 4.83(br s, 2H), 5.00-5.10(m, 2H), 7.00~7.76(m, 4H)

Preparation Example 170 : Synthesis of l-(2-chlorophenyl)-(S)-2-hydroxypropyl- (S)-l-carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Preparation Example 103, to obtain the title compound (0.34g, yield 10%).

1H NMR(400MHz, CDC1 ₃ ) 61.24(d, J = 6.8Hz, 3H), 2.13(d, J = 4.4Hz, 1H), 4.12~4.16(m, 1H), 4.85(br s, 2H), 5.98(d, J= 5.6Hz, 1H), 7.24~7.43(m, 4H)

Preparation Example 171 : Synthesis of l-(2-chlorophenyl)-(R)-2-hydroxypropyl- (R)-l-carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 2, to obtain the title compound (0.77g, yield

16%). 1H NMR(400MHz, CDCI3) 61.24(d, J = 6.4Hz, 3H), 2.04(d, J = 4.8Hz, 1H), 4.1 l~4.18(m, 1H), 4.74(br s, 2H), 6.00(d, J= 5.6Hz, 1H), 7.24~7.43(m, 4H)

Preparation Example 172 : Synthesis of l-(2-chlorophenyl)-2-hydroxypropyl-l- carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 3, to obtain the title compound (0.16g, yield 10-30%).

Ή NMR(400MHz, CDC1 ₃ ) 51.24(d, J = 6.4Hz, 3H), 2.04(d, J = 4.8Hz, 1H), 4.11~4.18(m, 1H), 4.74(br s, 2H), 6.00(d, J= 5.6Hz, 1H), 7.24~7.43(m, 4H)

Preparation Example 173 : Synthesis of l-(2-chlorophenyl)-(S)-2-hydroxypropyl- (S)-l-methylcarbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 15, to obtain the title compound (0.70g, yield 10-30%).

1H NMR(400MHz, CDC1 ₃ ) 61.21(d, J=6.4Hz, 3H), 2.80(d, J=4.8Hz, 3H), 3.12(s, 1H), 4.09~4.16(m, 1H), 4.86(br s, 1H), 5.99(d, J= 6.0Hz, 1H), 7.23~7.40(m, 4H)

Preparation Example 174 : Synthesis of l-(2-chlorophenyl)-(R)-2-hydroxypropyl- (R)-l-methylcarbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 22, to obtain the title compound (0.69g, yield 10-30%).

1H NMR(400MHz, CDC1 ₃ ) 51.21(d, J=6.4Hz, 3H), 2.80(d, J=4.8Hz, 3H), 3.12(s, 1H), 4.09~4.16(m, 1H), 4.86(br s, 1H), 5.99(d, J= 6.0Hz, 1H), 7.23~7.40(m, 4H)

Preparation Example 175 : Synthesis of l-(2-chlorophenyl)-2-hydroxypropyl-l- methylcarbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 29, to obtain the title compound (0.73g, yield 10%).

1H NMR(400MHz, CDC1 ₃ ) δ 1.22(d, J=6Hz, 3H), 2.15(d, J=4Hz, 1H), 2.8 l(d, J=5Hz, 3H), 4.12(dd, J=6Hz, IH), 4.83(br s, 1H), 6.00(d, J=6Hz, 1H), 7.23~7.41(m, 4H)

Preparation Example 176 : Synthesis of l-(2-chlorophenyl)-(S)-2-hydroxypropyl- (S)-l-propylcarbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 16, to obtain the title compound (0.15g, yield 10-30%).

Ή NMR(400MHz, CDC1 ₃ ) δ 0.91(t, J=7Hz, 3H), 1.22(d, J=6Hz, 3H), 1.52(dd, J=7Hz, 2H), 2.23(d, J=4Hz, 1H), 3.09~3.21(m, 2H), 4.09~4.17(m, 1H), 4.93(s, 1H), 5.99(d, J=6Hz, 1H), 7.23~7.47(m, 4H)

Preparation Example 177 : Synthesis of l-(2-chlorophenyl)-(R)-2-hydroxypropyl- (R)-l-propylcarbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 23, to obtain the title compound (0.04g, yield 10-30%).

1H NMR(400MHz, CDC1 ₃ ) δ 0.9 l(t, J=7Hz, 3H), 1.22(d, J=6Hz, 3H), 1.52(dd, J=7Hz, 2H), 2.23(d, J=4Hz, 1H), 3.09~3.21(m, 2H), 4.09~4.17(m, 1H), 4.93(s, 1H), 5.99(d, J=6Hz, 1H), 7.23~7.47(m, 4H)

Preparation Example 178 : Synthesis of l-(2-chlorophenyl)-2-hydroxypropyl-l- propylcarbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 30, to obtain the title compound (0.15g, yield 10%).

1H NMR(400MHz, CDC1 ₃ ) δ 0.9 l(t, J=7Hz, 3H), 1.22(d, J=6Hz, 3H), 1.52(dd, J=7Hz, 2H), 2.23(d, J=4Hz, 1H), 3.09~3.21(m, 2H), 4.09~4.17(m, 1H), 4.93(s, 1H), 5.99(d, J=6Hz, 1H), 7.23~7.47(m, 4H)

Preparation Example 179 : Synthesis of l-(2-chlorophenyl)-(S)-2-hydroxypropyl- (S)-l-isopropylcarbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 17, to obtain the title compound (0.42g, yield 28%).

1H NMR(400MHz, CDC1 ₃ ) 51.10(d, J=6.0Hz, 3H), 1.15~1.19(m, 6H), 2.41(s, 1H), 3.76~4.08(m, 1H), 4.34(s, 1H), 4.83(br s 1H), 5.95(d, J=5.3Hz, 1H), 7.19~7.39(m, 4H)

Preparation Example 180 : Synthesis of l-(2-chlorophenyl)-(R)-2-hydroxypropyl- (R)-l-isopropylcarbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 24, to obtain the title compound (0.5g, yield

10%).

1H NMR(400MHz, CDC1 ₃ ) 61.13(d, J=6Hz, 3H), 1.20(dd, J=9.2Hz, 6H), 2.23(s, 1H), 3.77~3.82(m, 1H), 4.10(s, 1H), 4.76(br s, 1H), 5.98(d, J=5.6Hz, 1H), 7.23~7.41(m, 4H)

Preparation Example 181 : Synthesis of l-(2-chlorophenyl)-2-hydroxypropyl-l- isopropylcarbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 31, to obtain the title compound (0.09g, yield 40%).

Ή NMR(400MHz, CDC1 ₃ ) δ 1.14(d, J=6Hz, 3H), 1.21(dd, J=6Hz, 6H), 2.16(d, J=5Hz, 1H), 3.81(t, J=6Hz, 1H), 4.11(d, J=5Hz, 1H), 4.73(br s, 1H), 5.98(d, J=5Hz, 1H), 7.24~741 (m, 4H)

Preparation Example 182 : Synthesis of l-(2-chlorophenyl)-(S)-2-hydroxypropyl- (S)-l-cyclopropylcarbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 18, to obtain the title compound (0.53g, yield 10-30%).

1H NMR(400MHz, CDC1 ₃ ) 50.53~0.60(m, 2H), 0.74(s, 2H), 1.21(d, J=6.0Hz, 3H), 2.19(s, 1H), 2.59(s, 1H), 4.11~4.15(m, 1H), 5.13(br s, 1H), 5.99(d, J=5.20Hz, 1H), 7.23~7.40(m, 4H)

Preparation Example 183 : Synthesis of l-(2-chlorophenyl)-(R)-2-hydroxypropyl- (R)-l-cycIopropylcarbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 25, to obtain the title compound (0.58g, yield

10%).

1H NMR(400MHz, CDC1 ₃ ) 50.53~0.60(m, 2H), 0.74(s, 2H), 1.21(d, J=6.0Hz, 3H), 2.19(s, 1H), 2.59(s, 1H), 4.11~4.15(m, 1H), 5.13(br s, 1H), 5.99(d, J=5.20Hz, 1H), 7.23~7.40(m, 4H)

Preparation Example 184 : Synthesis of l-(2-chlorophenyl)-2-hydroxypropyl-l- cyclopropylcarbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 32, to obtain the title compound (0.38g, yield

14%). 1H NMR(400MHz, CDC1 ₃ ) δ 0.71(s, 2H), 1.19(d, J=6Hz, 3H), 2.45(S, 1H), 2.57(S, 1H), 4.08~4.12(m, 1H), 5.26(s, 1H), 5.97(d, J=4Hz, 1H), 7.22~7.54(m, 4H)

Preparation Example 185 : Synthesis of l-(2-chlorophenyl)-(S)-2-hydroxypropyl- (S)-l-cyclohexylcarbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 19, to obtain the title compound (0.24g, yield 10-30%).

1H NMR(400MHz, CDC1 ₃ ) 61.10~1.39(m, 7H), 1.61(s, 3H), 1.71~1.74(m, 2H), 1.87(d, J=11.2Hz, 1H), 2.48(d, J=10.8Hz, 1H), 3.46(t, J=4Hz, 1H), 4.10~4.11(m, 1H), 4.80(br s 1H), 5.97(d, J=5.6Hz, 1H), 7.23~7.41(m, 4H)

Preparation Example 186 : Synthesis of l-(2-chlorophenyl)-(R)-2-hydroxypropyl- (R)-l-cyclohexylcarbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 26, to obtain the title compound (0.35g, yield 10%).

1H NMR(400MHz, CDC1 ₃ ) 51.10~1.39(m, 7H), 1.61(s, 3H), 1.71~1.74(m, 2H), 1.87(d, J=11.2Hz, 1H), 2.48(d, J=10.8Hz, 1H), 3.46(t, J=4Hz, 1H), 4.10~4.11(m, 1H), 4.80(br s 1H), 5.97(d, J=5.6Hz, 1H), 7.23~7.41(m, 4H)

Preparation Example 187 : Synthesis of l-(2-chlorophenyl)-2-hydroxypropyl-l- cyclohexylcarbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 33, to obtain the title compound (0.26g, yield 10%).

1H NMR(400MHz, CDC1 ₃ ) δ 1.12~1.19(m, 3H), 1.22(d, J=6Hz, 3H), 1.27~1.37(m, 1H), 1.71(t, J=6Hz, 2H), 1.86~1.88(m, 1H), 1.97~2.00(m, 1H), 2.18(d, J=4Hz, 1H), 3.47(S, 1H), 4.12(t, J=6Hz, 1H), 4.78(S, 1H), 5.97(d, J=6Hz, 1H), 7.23~7.40(m, 4H)

Preparation Example 188 : Synthesis of l-(2-chlorophenyI)-(S)-2-hydroxypropyl- (S)- 1 -benzylcarbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 20, to obtain the title compound (0.19g, yield 10-30%).

1H NMR(400MHz, CDC1 ₃ ) δ 1.23(d, J=6Hz, 3H), 2.16(d, J=4Hz, 1H), 4.12(t, J=6Hz, 1H), 4.31~4.44(m, 2H), 5.22(br S, 1H), 6.04(d, J=6Hz, 1H), 7.27~7.42(m, 9H)

Preparation Example 189 : Synthesis of l-(2-chlorophenyl)-(R)-2-hydroxypropyl- (R)-l-benzylcarbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 27, to obtain the title compound (0.07g, yield 10-30%).

1H NMR(400MHz, CDC1 ₃ ) δ 1.23(d, J=6Hz, 3H), 2.16(d, J=4Hz, 1H), 4.12(t, J=6Hz, 1H), 4.31~4.44(m, 2H), 5.22(br S, 1H), 6.04(d, J=6Hz, 1H), 7.27~7.42(m, 9H)

Preparation Example 190 : Synthesis of l-(2-chlorophenyl)-2-hydroxypropyl-l- benzylcarbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 34, to obtain the title compound (0.2 lg, yield 14%).

1H NMR(400MHz, CDC1 ₃ ) 6 1.23(d, J=6Hz, 3H), 2.16(d, J=4Hz, 1H), 4.12(t, J=6Hz, 1H), 4.31~4.44(m, 2H), 5.22(br S, 1H), 6.04(d, J=6Hz, 1H), 7.27~7.42(m, 9H)

Preparation Example 191 : Synthesis of l-(2,4-dichlorophenyl)-(S)-2- hydroxypropyl-(S)-l-carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 36, to obtain the title compound (0.05g, yield 10-30%).

1H NMR(400MHz, CDC1 ₃ ) 51.13(d, J = 6.8Hz, 3H), 2.49(d, J = 4.0Hz, 1H), 4.66~4.74(m, 1H), 4.76(br s, 2H), 6.20(d, J= 8.8Hz, 1H), 7.30(d, J=8.4Hz, 1H), 7.39(d, J=2.0Hz, 2H), 7.50(dd, J=8.4Hz, 2.0Hz, 1H)

Preparation Example 192 : Synthesis of l-(2,6-dichlorophenyl)-(S)-2- hydroxypropyl-(S)-l-carbamate

O 11

CI O NH ₂ A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 37, to obtain the title compound (0.07g, yield

24%).

1H NMR(400MHz, CDC1 ₃ ) 61.13(d, J - 6.8Hz, 3H), 2.49(d, J = 4.0Hz, 1H), 4.66~4.74(m, 1H), 4.76(br s, 2H), 6.20(d, J= 8.8Hz, 1H), 7.25~7.40(m, 3H)

Preparation Example 193 : Synthesis of l-(2,3-dichlorophenyl)-(S)-2- hydroxypropyl-(S)-l-carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 38, to obtain the title compound (0.08g, yield 10-30%).

1H NMR(400MHz, CDC1 ₃ ) 61.15(d, J = 6.4Hz, 3H), 3.66(d, J = 9.2Hz, 1H), 4.73(br s, 2H), 5.43(t, J= 9.0Hz, 1H), 5.62~5.69(m, 1H), 7.18~7.22(m, 3H),

Preparation Example 194 : Synthesis of l-(2,4-dichlorophenyl)-(S)-2-hydroxybutyl- (S)-l-carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 39, to obtain the title compound (0.07g, yield 10-30%).

1H NMR(400MHz, CDC1 ₃ ) 60.77(t, J = 7.4Hz, 3H), 0.92~1.01(m, 1H), 1.18~1.28(m, 1H), 4.06~4.13(m, 1H), 4.96(d, J = 6.0Hz, 1H), 5.91(d, J = 8.8Hz, 1H), 6.4(br s, 2H), 7.30~7.50(m, 3H)

Preparation Example 195 : Synthesis of l-(2,6-dichlorophenyl)-(S)-2- hydroxybutyl-( -l-carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 40, to obtain the title compound (0.1 lg, yield

29%).

1H NMR(400MHz, CDC1 ₃ ) 50.77(t, J = 7.4Hz, 3H), 0.92~1.01(m, 1H), 1.18~1.28(m, 1H), 4.06~4.13(m, 1H), 4.96(d, J=6.0Hz, 1H), 5.91(d, J=8.8Hz, 1H), 6.4(br s, 2H), 7.25~7.40(m, 3H)

Preparation Example 196 : Synthesis of l-(2,4-dichlorophenyl)-(S)-2-hydroxy-3- methyl-butyl-(S)-l-carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 41, to obtain the title compound (O.Olg, yield 10-30%).

1H NMR(400MHz, CDC1 ₃ ) 61.00(t, J = 7.2Hz, 6H), 1.73~1.79(m, 1H), 3.67~3.69(m, 1H), 4.96(d, J=6.0Hz, 1H), 5.91(d, J=8.8Hz, 1H), 6.42(br s, 2H), 7.30~7.50(m, 3H)

Preparation Example 197 : Synthesis of l-(2,6-dichlorophenyl)-(S)-2-hydroxy-3- methyl-butyl-(S)-l-carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 42, to obtain the title compound (0.03g, yield

10-30%). 1H NMR(400MHz, CDC1 ₃ ) 61.00(t, J = 7.2Hz, 6H), 1.73~1.79(m, 1H), 3.67~3.69(m, 1H), 4.96(d, J=6.0Hz, 1H), 5.91(d, J=8.8Hz, 1H), 6.42(br s, 2H), 7.25~7.40(m, 3H)

Preparation Example 198 : Synthesis of l-(2,4-dichlorophenyI)-(S)-2-hydroxyhexyl- (S)-l-carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 43, to obtain the title compound (0.2 lg, yield 10-30%).

1H NMR(400MHz, CDC1 ₃ ) 60.85(t, J=7.2Hz, 3H), 1.18~1.33(m, 4H), 1.48~1.55(m, 2H), 2.35(d, J=4.4Hz, 1H), 4.45~4.50(m, 1H), 4.76(br s, 2H), 6.21(d, J=8.4Hz, 1H), 7.30~7.50(m, 3H)

Preparation Example 199 : Synthesis of l-(2,6-dichlorophenyl)-(S)-2-hydroxyhexyl- (S)-l-carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 44, to obtain the title compound (0.06g, yield

29%).

1H NMR(400MHz, CDC1 ₃ ) 60.85(t, J = 7.2Hz, 3H), 1.18~1.33(m, 4H), 1.48~1.55(m, 2H), 2.35(d, J = 4.4Hz, 1H), 4.45~4.50(m, 1H), 4.76(br s, 2H), 6.21(d, J=8.4Hz, 1H), 7.16~7.34(m, 3H)

Preparation Example 200 : Synthesis of l-(2,4-dichlorophenyl)-(R)-2- hydroxypropyl-(R)-l-carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 45, to obtain the title compound (0.04g, yield 10-30%).

Ή NMR(400MHz, CDC1 ₃ ) 51.13(d, J=6.8Hz, 3H), 2.49(d, J=4.0Hz, 1H), 4.66~4.74(m, 1H), 4.76(br s, 2H), 6.20(d, J=8.8Hz, 1H), 7.30~7.50(m, 3H)

Preparation Example 201 : Synthesis of l-(2,6-dichlorophenyl)-(R)-2- hydroxypropyl-(R)-l-carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 46, to obtain the title compound (0.09g, yield 10-30%).

1H NMR(400MHz, CDC1 ₃ ) 51.13(d, J = 6.8Hz, 3H), 2.49(d, J = 4.0Hz, 1H), 4.66~4.74(m, 1H), 4.76(br s, 2H), 6.20(d, J= 8.8Hz, 1H), 7.25~7.40(m, 3H)

Preparation Example 202 : Synthesis of l-(2,3-dichlorophenyl)-(R)-2- hydroxypropyl-(R)-l-carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 47, to obtain the title compound (0.25g, yield 10-30%).

Ή NMR(400MHz, CDC1 ₃ ) 51.15(d, J = 6.4Hz, 3H), 3.66(d, J = 9.2Hz, 1H), 4.73(br s, 2H), 5.43(t, J= 9.0Hz, 1H), 5.62~5.69(m, 1H), 7.18-7.22(m, 3H), Preparation Example 203 : Synthesis of l-(2,4-dichlorophenyI)-(R)-2-hydroxybutyl- (R)-l-carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 48, to obtain the title compound (0.08g, yield 10-30%).

1H NMR(400MHz, CDC1 ₃ ) 60.77(t, J = 7.4Hz, 3H), 0.92~1.01(m, 1H), 1.18~1.28(m, 1H), 4.06~4.13(m, 1H), 4.96(d, J = 6.0Hz, 1H), 5.91(d, J = 8.8Hz, 1H), 6.4(br s, 2H), 7.30~7.50(m, 3H)

Preparation Example 204 : Synthesis of l-(2,6-dichlorophenyl)-(R)-2- hydroxybutyl-(R)-l-carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 49, to obtain the title compound (0.09g, yield 10-30%). Ή NMR(400MHz, CDC1 ₃ ) 60.77(t, J= 7.4Hz, 3H), 0.92~1.01(m, 1H), 1.18~1.28(m, 1H), 4.06~4.13(m, 1H), 4.96(d, J = 6.0Hz, 1H), 5.91(d, J = 8.8Hz, 1H), 6.4(br s, 2H), 7.25~7.40(m, 3H)

Preparation Example 205 : Synthesis of l-(2,4-dichlorophenyl)-(R)-2-hydroxy-3- methyl-butyl-(R)-l-carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 50, to obtain the title compound (O.Olg, yield 10-30%).

Ή NMR(400MHz, CDC1 ₃ ) 51.00(t, J = 7.2Hz, 6H), 1.73~1.79(m, 1H), 3.67~3.69(m, 1H), 4.96(d, J=6.0Hz, 1H), 5.91(d, J=8.8Hz, 1H), 6.42(br s, 2H), 7.30~7.50(m, 3H)

Preparation Example 206 : Synthesis of l-(2,6-dichlorophenyl)-(R)-2-hydroxy-3- methyl-butyl-(R)-l-carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 51, to obtain the title compound (O.Olg, yield 10-30%).

1H NMR(400MHz, CDC1 ₃ ) 61.00(t, J = 7.2Hz, 6H), 1.73~1.79(m, 1H), 3.67~3.69(m, 1H), 4.96(d, J=6.0Hz, 1H), 5.91(d, J=8.8Hz, 1H), 6.42(br s, 2H), 7.25~7.40(m, 3H)

Preparation Example 207 : Synthesis of l-(2,4-dichlorophenyl)-(R)-2- hydroxyhexyl-(R)-l-carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 52, to obtain the title compound (0.2 lg, yield 10-30%).

Ή NMR(400MHz, CDC1 ₃ ) 50.85(t, J=7.2Hz, 3H), 1.18~1.33(m, 4H), 1.48~1.55(m, 2H), 2.35(d, J=4.4Hz, 1H), 4.45~4.50(m, 1H), 4.76(br s, 2H), 6.21(d, J=8.4Hz, 1H), 7.30~7.50(m, 3H)

Preparation Example 208 : Synthesis of l-(2,6-dichlorophenyl)-(R)-2- hydroxyhexyl-(R)-l-carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 53, to obtain the title compound (0.12g, yield 10-30%).

Ή NMR(400MHz, CDC1 ₃ ) 50.85(t, J = 7.2Hz, 3H), 1.18~1.33(m, 4H), 1.48~1.55(m, 2H), 2.35(d, J = 4.4Hz, 1H), 4.45~4.50(m, 1H), 4.76(br s, 2H), 6.21(d, J = 8.4Hz, 1H), 7.16~7.34(m, 3H)

Preparation Example 209 : Synthesis of l-(2,4-dichlorophenyl)-2-hydroxypropyl-l- carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 54, to obtain the title compound (0.05g, yield 10-30%).

1H NMR(400MHz, CDC1 ₃ ) 51.13(d, J=6.8Hz, 3H), 2.49(d, J=4.0Hz, 1H), 4.66~4.74(m, 1H), 4.76(br s, 2H), 6.20(d, J=8.8Hz, 1H), 7.30~7.50(m, 3H)

Preparation Example 210 : Synthesis of l-(2,6-dichlorophenyl)-2-hydroxypropyl-l- carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 55, to obtain the title compound (0.06g, yield

10-30%).

1H NMR(400MHz, CDC1 ₃ ) 61.13(d, J = 6.8Hz, 3H), 2.49(d, J = 4.0Hz, 1H), 4.66~4.74(m, 1H), 4.76(br s, 2H), 6.20(d, J= 8.8Hz, 1H), 7.25~7.40(m, 3H)

Preparation Example 211 : Synthesis of l-(2,3-dichlorophenyl)-(R)-2- hydroxypropyl-(R)-l-carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 56, to obtain the title compound (0.02g, yield 10-30%).

1H NMR(400MHz, CDC1 ₃ ) 61.15(d, J = 6.4Hz, 3H), 3.66(d, J = 9.2Hz, 1H), 4.73(br s, 2H), 5.43(t, J= 9.0Hz, 1H), 5.62~5.69(m, 1H), 7.18~7.22(m, 3H),

Preparation Example 212 : Synthesis of l-(2,4-dichlorophenyl)-2-hydroxybutyl-l- carba

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 57, to obtain the title compound (0.07g, yield 10-30%).

1H NMR(400MHz, CDC1 ₃ ) 60.77(t, J=7.4Hz, 3H), 0.92~1.01(m, 1H), 1.18~1.28(m, 1H), 4.06~4.13(m, 1H), 4.96(d, J=6.0Hz, 1H), 5.91(d, J=8.8Hz, 1H), 6.4(br s, 2H), 7.30~7.50(m, 3H)

Preparation Example 213 : Synthesis of l-(2,6-dichlorophenyl)-2-hydroxybutyl-l- carba

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 58, to obtain the title compound (0.1 Og, yield 10-30%).

1H NMR(400MHz, CDC1 ₃ ) 60.77(t, J = 7.4Hz, 3H), 0.92~1.01(m, 1H), 1.18~1.28(m, 1H), 4.06~4.13(m, 1H), 4.96(d, J = 6.0Hz, 1H), 5.91(d, J = 8.8Hz, 1H), 6.4(br s, 2H), 7.25~7.40(m, 3H)

Preparation Example 214 : Synthesis of l-(2,4-dichlorophenyl)-2-hydroxy-3- methyl-butyl-l-carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 59, to obtain the title compound (0.04g, yield 10-30%).

1H NMR(400MHz, CDC1 ₃ ) 51.00(t, J = 7.2Hz, 6H), 1.73~1.79(m, 1H), 3.67~3.69(m, 1H), 4.96(d, J=6.0Hz, 1H), 5.91(d, J=8.8Hz, 1H), 6.42(br s, 2H), 7.30~7.50(m, 3H)

Preparation Example 215 : Synthesis of l-(2,6-dichlorophenyl)-2-hydroxy-3- methyl-butyl-l-carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 60, to obtain the title compound (0.01 g, yield

10-30%).

1H NMR(400MHz, CDC1 ₃ ) 51.00(t, J = 7.2Hz, 6H), 1.73~1.79(m, 1H), 3.67~3.69(m, 1H), 4.96(d, J=6.0Hz, 1H), 5.91(d, J=8.8Hz, 1H), 6.42(br s, 2H), 7.25~7.40(m, 3H)

Preparation Example 216 : Synthesis of l-(2,4-dichlorophenyl)-2-hydroxyhexyl-l- carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 61, to obtain the title compound (0.2 lg, yield 10-30%).

1H NMR(400MHz, CDC1 ₃ ) 50.85(t, J=7.2Hz, 3H), 1.18~1.33(m, 4H), 1.48~1.55(m, 2H), 2.35(d, J=4.4Hz, lH), 4.45~4.50(m, 1H), 4.76(br s, 2H), 6.21(d, J=8.4Hz, 1H), 7.30~7.50(m, 3H)

Preparation Example 217 : Synthesis of l-(2,6-dichlorophenyl)-2-hydroxyhexyl-l- carbamate

A regioisomer of monocarbamate was separated and purified by conducting the silica gel column chromatography as described in Example 62, to obtain the title compound (0.12g, yield 10-30%).

1H NMR(400MHz, CDC1 ₃ ) 50.85(t, J = 7.2Hz, 3H), 1.18~1.33(m, 4H), 1.48~1.55(m, 2H), 2.35(d, J = 4.4Hz, 1H), 4.45~4.50(m, 1H), 4.76(br s, 2H), 6.21(d, J = 8.4Hz, 1H), 7.16~7.34(m, 3H)

Preparation Example 218 : Synthesis of l-(2-iodophenyl)-(S)-l-hydroxy-3-methyl- butyl-(S)-2-carbamate

The substantially same method as described in Example 169 was conducted, except that l-(2-iodophenyl)-3-methyl-(S,S)-l,2-butanediol(Preparation example 83) was used instead of 1- (2-iodophenyl)-(S,S)-l,2-butanediol(Preparation Example 68), to obtain the title compound (1.92g, yield 20-50%).

1H NMR(400MHz, CDC1 ₃ ) 60.97(d, J=6.4Hz, 6H), 2.36~2.52(m, 1H), 3.34(s, 1H), 4.80(br s 2H), 5.04(t, J=12.5Hz, 1H), 5.14(s, 1H), 7.01~7.63(m, 4H)

Preparation Example 219 : Synthesis of l-(2-iodophenyl)-(S)-l-hydroxyhexyl-(S)-2- carbam

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2-iodophenyl)-(S,S)-l ,2-hexanediol obtained in Preparation Example 85 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (1.68g, yield 30-60%).

1H NMR(400MHz, CDC1 ₃ ) 60.84(t, J = 7.0Hz, 3H), 1.20~1.35(m, 4H), 1.36~1.41(m, lH), 1.59~1.63(m, 1H), 3.71(d, J = 10.0Hz, 1H), 4.74(br s, 2H), 5.40~5.44(m, 1H), 5.52~5.57(m, 1H), 6.96~7.57(m, 4H)

Preparation Example 220: Synthesis of l-(2-iodophenyl)-(S)-l-hydroxypropyl-(S)- 2-methylcarbamate

The substantially same method as described in Example 117 was conducted, except that l-(2-iodophenyl)-(S,S)-l,2-propandiol(Preparation example 66) was used instead of l-(2- chlorophenyl)-(S,S)-l,2-propandiol(Preparation example 14), to obtain the title compound (l .Olg, yield 20-50%).

1H NMR(400MHz, CDC1 ₃ ) 51.03~1.25(m, 3H), 2.76(s, 3H), 3.34(s, 1H), 4.80(br s 1H), 5.04(t, J=12.5Hz, 1H), 5.14(s, 1H), 7.01~7.63(m, 4H)

Preparation Example 221: Synthesis of l-(2-iodophenyl)-(S)-l-hydroxypropyl-(S)- 2-propylcarbamate

The substantially same method as described in Example 118 was conducted, except that

1- (2-iodophenyl)-(S,S)-l,2-propandiol(Preparation example 66) was used instead of l-(2- chlorophenyl)-(S,S)-l,2-propandiol(Preparation example 14), to obtain the title compound (0.72g, yield 20-50%).

l NMR(400MHz, CDC1 ₃ ) 50.90(t, J=6.8Hz, 3H), 1.20(d, J=5.96Hz, 3H), 1.49(dd, J=14.2Hz, 2H), 3.11(d, J=6.28Hz, 2H), 3.34(s, IH), 4.84(br s, IH), 5.05(t, J=5.88Hz, IH), 5.14(s, IH), 7.02~7.63(m, 4H)

Preparation Example 222: Synthesis of l-(2-iodophenyi)-(S)-l-hydroxypropyl-(S)-

2- isopropylcarbamate

The substantially same method as described in Example 119 was conducted, except that

1- (2-iodophenyl)-(S,S)-l,2-propandiol(Preparation example 66) was used instead of l-(2- chlorophenyl)-(S,S)-l,2-propandiol(Preparation example 14), to obtain the title compound (1.08g, yield 20-50%).

Ή NMR(400MHz, CDC1 ₃ ) 51.14(dd, J=6.5Hz, 6H), 1.19(d, J=6.4Hz, 3H), 3.21(s, IH), 3.73~3.82(m, IH), 4.59(br s, IH), 5.01~5.07(m, IH), 5.14(t, J=5.8Hz, IH), 7.01~7.65(m, 4H)

Preparation Example 223 : Synthesis of l-(2-iodophenyl)-(S)-l-hydroxypropyl-(S)-

2- cyclopropylcarbamate

The substantially same method as described in Example 120 was conducted, except that

1- (2-iodophenyl)-(S,S)-l,2-propandiol(Preparation example 66) was used instead of l-(2- chlorophenyl)-(S,S)-l,2-propandiol(Preparation example 14), to obtain the title compound (1.02g, yield 20-50%).

Ή NMR(400MHz, CDC1 ₃ ) 60.50~0.56(m, 2H), 0.74(d, J=7.21Hz, 2H), 1.25(s, 3H), 2.56~2.61(m, IH), 3.72(s, IH), 4.98(br s, IH), 5.05~5.11(m, IH), 7.16(s, IH), 7.03~7.64(m, 4H)

Preparation Example 224 : Synthesis of l-(2-iodophenyl)-(S)-l-hydroxypropyl-(S)-

2- cyclohexyl carbamate

The substantially same method as described in Example 121 was conducted, except that

1- (2-iodophenyl)-(S,S)-l,2-propandiol(Preparation example 66) was used instead of l-(2- chlorophenyl)-(S,S)-l,2-propandiol(Preparation example 14), to obtain the title compound (1.84g, yield 20-50%).

1H NMR(400MHz, CDC1 ₃ ) 81.06~1.40(m, 7H), 1.56~1.61(m, 2H), 1.69~1.71(m, 2H), 1.87~1.94(m, 2H), 3.19(d, J=4.32Hz, IH), 3.45(s, IH), 4.64(br s IH), 5.02~5.07(m, IH), 5.14(t, J=6.08Hz, IH) 7.02~7.63(m, 4H)

Preparation Example 225 : Synthesis of l-(2-iodophenyl)-(S)-l-hydroxypropyl-(S)-

2- benzyl carbamate

The substantially same method as described in Example 122 was conducted, except that l-(2-iodophenyl)-(S,S)-l,2-propandiol(Preparation example 66) was used instead of l-(2- chlorophenyl)-(S,S)-l,2-propandiol(Preparation example 14), to obtain the title compound (0.72g, yield 20-50%).

Ή NMR(400MHz, CDC1 ₃ ) δ 1.27(d, J=10Hz, 3H), 3.12(d, J=5Hz, IH), 4.37(d, J=6Hz, 2H), 5.12~5.19(m, 3H), 7.05~7.66(m, 9H) Preparation Example 226 : Synthesis of l-(2-chlorophenyl)-(S)-l-hydroxypropyl- (S)-2-bicyclo[2,2,l]heptanescarbamate

The substantially same method as described in Example 123 was conducted, except that

1- (2-iodophenyl)-(S,S)-l ,2-propandiol(Preparation example 66) was used instead of l-(2- chlorophenyl)-(S,S)-l,2-propandiol(Preparation example 14), to obtain the title compound (0.82g, yield 20-50%).

1H NMR(400MHz, CDC1 ₃ ) 81.08~1.35(m, 9H), 1.65(br s, 1H), 1.75~1.71(m, 1H), 2.14~2.24(m, 1H), 2.27~2.30(m, 1H), 3.23~3.29(m, 1H), 3.47~3.52(m, 1H), 4.67(br s, 1H), 5.01~5.09(m, 1H), 5.12~5.18(m, 1H), 7.02~7.65(m, 4H)

Preparation Example 227: Synthesis of l-(2-fluorophenyl)-(S)-l-hydroxypropyl-(S)-

2- methylcarbamate

The substantially same method as described in Example 220 was conducted, except that

1- (2-fluorophenyl)-(S,S)-l,2-propandiol(Preparation example 61) was used instead of l-(2- iodophenyl)-(S,S)-l,2-propandiol(Preparation example 66), to obtain the title compound (1.19g, yield 20-50%).

lU NMR(400MHz, CDC1 ₃ ) δ1.03~1.25(πι, 3H), 2.76(s, 3H), 3.34(s, 1H), 4.80(br s 1H), 5.04(t, J=12.5Hz, 1H), 5.14(s, 1H), 6.90-7.50(m, 4H)

Preparation Example 228: Synthesis of l-(2-fluorophenyl)-(S)-l-hydroxypropyl-(S)-

2- propylcarbamate

The substantially same method as described in Example 221 was conducted, except that

1- (2-fluorophenyl)-(S,S)-l,2-propandiol(Preparation example 61) was used instead of l -(2- iodophenyl)-(S,S)-l,2-propandiol(Preparation example 66), to obtain the title compound (0.86g, yield 20-50%).

1H NMR(400MHz, CDC1 ₃ ) 60.90(t, J=6.8Hz, 3H), 1.20(d, J=5.96Hz, 3H), 1.49(dd, J=14.2Hz, 2H), 3.11(d, J=6.28Hz, 2H), 3.34(s, IH), 4.84(br s, IH), 5.05(t, J=5.88Hz, IH), 5.14(s, IH), 6.99~7.53(m, 4H)

Preparation Example 229: Synthesis of l-(2-fuIorophenyl)-(S)-l-hydroxypropyl-(S)-

2- isopropylcarbamate

The substantially same method as described in Example 222 was conducted, except that l-(2-fluorophenyl)-(S,S)-l,2-propandiol(Preparation example 61) was used instead of l-(2- iodophenyl)-(S,S)-l,2-propandiol(Preparation example 66), to obtain the title compound (0.48g, yield 20-50%).

Ή NMR(400MHz, CDC1 ₃ ) 61.14(dd, J=6.5Hz, 6H), 1.19(d, J=6.4Hz, 3H), 3.21(s, IH), 3.73~3.82(m, IH), 4.59(br s, IH), 5.01~5.07(m, IH), 5.14(t, J=5.8Hz, IH), 7.01~7.62(m, 4H)

Preparation Example 230 : Synthesis of l-(2-fluorophenyl)-(S)-l-hydroxypropyl- (S)-2-cyclopropylcarbamate

The substantially same method as described in Example 223 was conducted, except that l-(2-fluorophenyl)-(S,S)-l,2-propandiol(Preparation example 61) was used instead of l-(2- iodophenyl)-(S,S)-l,2-propandiol(Preparation example 66), to obtain the title compound (0.39g, yield 20-50%)

Ή NMR(400MHz, CDC1 ₃ ) 50.50~0.56(m, 2H), 0.74(d, J=7.21Hz, 2H), 1.25(s, 3H), 2.56~2.61(m, 1H), 3.72(s, 1H), 4.98(br s, 1H), 5.05-5. l l(m, 1H), 7.16(s, 1H), 7.01~7.65(m, 4H)

Preparation Example 231 : Synthesis of l-(2-fluorophenyI)-(S)-l-hydroxypropyl- (S)-2-cyclohexyl carbamate

The substantially same method as described in Example 225 was conducted, except that l-(2-fluorophenyl)-(S,S)-l,2-propandiol(Preparation example 61) was used instead of l-(2- iodophenyl)-(S,S)-l,2-propandiol(Preparation example 66), to obtain the title compound (0.54g, yield 20-50%)

1H NMR(400MHz, CDC1 ₃ ) 51.06~1.40(m, 7H), 1.56~1.61(m, 2H), 1.69~1.71(m, 2H), 1.87-1.94(m, 2H), 3.19(d, J=4.32Hz, 1H), 3.45(s, 1H), 4.64(br s 1H), 5.02~5.07(m, 1H), 5.14(t, J=6.08Hz, 1H) 7.00~7.65(m, 4H)

Preparation Example 232 : Synthesis of l-(2-fluorophenyl)-(S)-l-hydroxypropyl- (S)-2-benzyl carbamate

The substantially same method as described in Example 226 was conducted, except that l-(2-fluorophenyl)-(S,S)-l,2-propandiol(Preparation example 61) was used instead of l -(2- iodophenyl)-(S,S)-l,2-propandiol(Preparation example 66), to obtain the title compound (0.39g, yield 20-50%)

Ή NMR(400MHz, CDC1 ₃ ) δ 1.27(d, J=10Hz, 3H), 3.12(d, J=5Hz, 1H), 4.37(d, J=6Hz, 2H), 5.12-5.19(m, 3H), 7.01~7.67(m, 9H) Preparation Example 233 : Synthesis of l-(2-fluorophenyI)-(S)-l-hydroxypropyl- (S)-2-bicycIo[2,2,l]heptanescarbamate

The substantially same method as described in Example 227 was conducted, except that l-(2-fluorophenyl)-(S,S)-l,2-propandiol(Preparation example 61) was used instead of l-(2- iodophenyl)-(S,S)-l,2-propandiol(Preparation example 66), to obtain the title compound (0.57g, yield 20-50%)

1H NMR(400MHz, CDC1 ₃ ) 51.08~1.35(m, 9H), 1.65(br s, 1H), 1.75~1.71(m, 1H), 2.14~2.24(m, l _. H), 2.27~2.30(m, 1H), 3.23~3.29(m, 1H), 3.47~3.52(m, 1H), 4.67(br s, 1H), 5.01~5.09(m, 1H), 5.12~5.18(m, 1H), 7.01~7.66(m, 4H)

Preparation Example 234: Synthesis of l-(2-iodophenyl)-(S)-l-hydroxybutyl-(S)-2- methylcarbamate

The substantially same method as described in Example 117 was conducted, except that l-(2-iodophenyl)-(S,S)-l,2-butanediol(Preparation example 68) was used instead of l-(2- iodophenyl)-(S,S)-l,2-propandiol(Preparation example 66), to obtain the title compound (1.81g, yield 20-50%).

1H NMR(400MHz, CDCI3) 80.97(d, J=6.4Hz, 3H), 1.56(m, 2H), 2.76(s, 3H), 3.34(s, 1H), 4.80(br s 1H), 5.04(t, J=12.5Hz, 1H), 5.14(s, 1H), 7.01-7.63(m, 4H)

Preparation Example 235 : Synthesis of l-(2-iodophenyl)-(S)-l-hydroxybutyl-(S)-2- propylcarbamate

The substantially same method as described in Example 118 was conducted, except that l-(2-iodophenyl)-(S,S)-l,2-butanediol(Preparation example 68) was used instead of l-(2- iodophenyl)-(S,S)-l,2-propandiol(Preparation example 66), to obtain the title compound (0.92g, yield 20-50%).

Ή NMR(400MHz, CDC1 ₃ ) 50.90(t, J=6.8Hz, 3H), 1.20(d, J=5.96Hz, 3H), 1.49(dd, J=14.2Hz, 2H), 1.57(m, 2H), 3.11(d, J=6.28Hz, 2H), 3.34(s, 1H), 4.84(br s, 1H), 5.05(t, J=5.88Hz, 1H), 5.14(s, 1H), 7.02~7.63(m, 4H)

Preparation Example 236: Synthesis of l-(2-iodophenyl)-(S)-l-hydroxybutyl-(S)-2- isopropylcarbamate

The substantially same method as described in Example 119 was conducted, except that l-(2-iodophenyl)-(S,S)-l,2-butanediol(Preparation example 68) was used instead of l-(2- chlorophenyl)-(S,S)-l,2-propandiol(Preparation example 14), to obtain the title compound (1.28g, yield 20-50%).

Ή NMR(400MHz, CDC1 ₃ ) 50.96(t, J=6.8Hz, 3H), 1.14(dd, J=6.5Hz, 6H), 1.57(m, 2H), 3.21(s, 1H), 3.73~3.82(m, 1H), 4.59(br s, 1H), 5.01~5.07(m, 1H), 5.14(t, J=5.8Hz, 1H), 7.01~7.65(m, 4H)

Preparation Example 237 : Synthesis of l-(2-iodophenyl)-(S)-l-hydroxybutyl-(S)-2- cyclopropylcarbamate

The substantially same method as described in Example 120 was conducted, except that l-(2-iodophenyl)-(S,S)-l,2-butanediol(Preparation example 68) was used instead of l-(2- chlorophenyl)-(S,S)-l,2-propandiol(Preparation example 14), to obtain the title compound (1.51g, yield 20-50%).

1H NMR(400MHz, CDC1 ₃ ) 60.50~0.56(m, 2H), 0.74(d, J=7.21Hz, 2H), 0.96(t, J=6.8Hz, 3H), 1.25(m, 2H), 2.56~2.61(m, 1H), 3.72(s, 1H), 4.98(br s, 1H), 5.05~5.11(m, 1H), 7.16(s, 1H), 6.96~7.57(m, 4H)

Preparation Example 238 : Synthesis of l-(2-iodophenyl)-(S)-l-hydroxybutyl-(S)-2- cyclohexyl carbamate

The substantially same method as described in Example 121 was conducted, except that l-(2-iodophenyl)-(S,S)-l,2-butanediol(Preparation example 68) was used instead of l-(2- chlorophenyl)-(S,S)-l,2-propandiol(Preparation example 14), to obtain the title compound (1.92g, yield 20-50%).

Ή NMPv(400MHz, CDC1 ₃ ) 60.96(t, J=6.8Hz, 3H), 1.06~1.40(m, 7H), 1.56~1.61(m, 2H), 1.69~1.71(m, 2H), 1.87~1.94(m, 2H), 3.19(d, J=4.32Hz, 1H), 3.45(s, 1H), 4.64(br s 1H), 5.02~5.07(m, 1H), 5.14(t, J=6.08Hz, lH) 7.02~7.63(m, 4H)

Preparation Example 239 : Synthesis of l-(2-iodophenyl)-(S)-l-hydroxybutyl-(S)-2- benzyl carbamate

The substantially same method as described in Example 122 was conducted, except that l-(2-iodophenyl)-(S,S)-l,2-butanediol(Preparation example 68) was used instead of l-(2- chlorophenyl)-(S,S)-l,2-propandiol(Preparation example 14), to obtain the title compound

(1.52g, yield 20-50%).

1H NMR(400MHz, CDC1 ₃ ) δ 0.96(t, J=6.8Hz, 3H), 1.55~1.62(m, 2H), 3.12(d, J=5Hz, 1H), 4.37(d, J=6Hz, 2H), 5.12~5.19(m, 3H), 7.05~7.66(m, 9H)

Preparation Example 240 : Synthesis of l-(2-chlorophenyl)-(S)-l-hydroxybutyl-(S)- 2-bicyclo[2,2,l]heptanescarbamate

The substantially same method as described in Example 123 was conducted, except that l-(2-iodophenyl)-(S,S)-l,2-butanediol(Preparation example 68) was used instead of l-(2- chlorophenyl)-(S,S)-l,2-propandiol(Preparation example 14), to obtain the title compound (1.08g, yield 20-50%).

1H NMR(400MHz, CDC1 ₃ ) 60.96(t, J=6.8Hz, 3H), 1.08~1.35(m, 6H), 1.55~1.62(m, 2H), 1.65(br s, 1H), 1.75~1.71(m, 1H), 2.14~2.24(m, 1H), 2.27~2.30(m, 1H), 3.23~3.29(m, 1H), 3.47~3.52(m, 1H), 4.67(br s, 1H), 5.01~5.09(m, 1H), 5.12~5.18(m, 1H), 7.02~7.65(m, 4H)

Preparation Example 241: Synthesis of l-(2-iodophenyl)-(S)-l-hydroxy-3-methyl- butyl-(S)-2-methylcarbamate

The substantially same method as described in Example 117 was conducted, except that l-(2-iodophenyl)-3-methyl-(S,S)-l,2-butanediol(Preparation example 83) was used instead of 1- (2-iodophenyl)-(S,S)-l,2-propandiol(Preparation example 66), to obtain the title compound (1.92g, yield 20-50%).

1H NMR(400MHz, CDCI ₃ ) 50.97(d, J=6.4Hz, 6H), 2.36~2.52(m, 1H), 2.76(s, 3H), 3.34(s, 1H), 4.80(br s 1H), 5.04(t, J=12.5Hz, 1H), 5.14(s, 1H), 7.01~7.63(m, 4H)

Preparation Example 242 : Synthesis of l-(2-iodophenyl)-(S)-l-hydroxy-3-methyl- butyl-(S)-2-propylcarbamate

The substantially same method as described in Example 118 was conducted, except that l-(2-iodophenyl)-3-methyl-(S,S)-l,2-butanediol(Preparation example 83) was used instead of 1- (2-iodophenyl)-(S,S)-l ,2-propandiol(Preparation example 66), to obtain the title compound (1.82g, yield 20-50%).

1H NMR(400MHz, CDC1 ₃ ) 50.96(t, J=6.8Hz, 3H), 1.10(d, J=6.4Hz, 6H), 1.49(dd, J=14.2Hz, 2H), 2.38~2.42(m, 1H), 3.11(d, J=6.28Hz, 2H), 3.34(s, 1H), 4.84(br s, 1H), 5.05(t, J=5.88Hz, 1H), 5.14(s, 1H), 7.02~7.63(m, 4H)

Preparation Example 243: Synthesis of l-(2-iodophenyi)-(S)-l-hydroxy-3-methyl- butyI-(S)-2-isopropylcarbamate

The substantially same method as described in Example 119 was conducted, except that l-(2-iodophenyl)-3-methyl-(S,S)-l,2-butanediol(Preparation example 83) was used instead of 1- (2-chlorophenyl)-(S,S)-l,2-propandiol(Preparation example 14), to obtain the title compound (1.77g, yield 20-50%).

Ή NMR(400MHz, CDC1 ₃ ) 51.01(d, J=6.8Hz, 6H), 1.14(d, J=6.5Hz, 6H), 2.39~2.47(m, 1H), 3.90~3.98(m, 1H), 3.73~3.82(m, 1H), 4.59(br s, 1H), 5.01~5.07(m, 1H), 5.14(t, J=5.8Hz, 1H), 7.01~7.65(m, 4H)

Preparation Example 244 : Synthesis of l-(2-iodophenyl)-(S)-l-hydroxy-3-methyl- butyl-(S)-2-cyclopropylcarbamate

The substantially same method as described in Example 120 was conducted, except that l-(2-iodophenyl)-3-methyl-(S,S)-l,2-butanediol(Preparation example 83) was used instead of 1- (2-chlorophenyl)-(S,S)-l,2-propandiol(Preparation example 14), to obtain the title compound (1.81g, yield 20-50%).

1H NMR(400MHz, CDC1 ₃ ) 50.50~0.56(m, 2H), 0.74(d, J=7.21Hz, 2H), 1.01(d, J=6.8Hz, 6H), 2.38~2.44(m, 1H), 2.56~2.61(m, 1H), 3.72(s, 1H), 4.98(br s, 1H), 5.05~5.11(m, 1H), 7.16(s, 1H), 6.96~7.57(m, 4H)

Preparation Example 245 : Synthesis of l-(2-iodophenyI)-(S)-l-hydroxy-3-methyl- butyI-(S)-2-cycIohexyl carbamate

The substantially same method as described in Example 121 was conducted, except that l-(2-iodophenyl)-3-methyl-(S,S)-l,2-butanediol(Preparation example 83) was used instead of 1- (2-chlorophenyl)-(S,S)-l,2-propandiol(Preparation example 14), to obtain the title compound (1.29g, yield 20-50%).

1H NMR(400MHz, CDC1 ₃ ) 61.01(d, J=6.8Hz, 6H), l .l l~1.21(m, 4H), 1.47~1.49(m, 4H), 1.69~1.71(m, 2H), 2.38~2.44(m, 1H), 3.19(d, J=4.32Hz, 1H), 3.45(s, 1H), 4.64(br s 1H), 5.02~5.07(m, 1H), 5.14(t, J=6.08Hz, 1H) 7.02~7.63(m, 4H)

Preparation Example 246 : Synthesis of l-(2-iodophenyl)-(S)-l-hydroxy-3-methyl- butyl-(S)-2-benzyl carbamate

The substantially same method as described in Example 122 was conducted, except that l-(2-iodophenyl)-(S,S)-l,2-butanediol(Preparation example 68) was used instead of l-(2- chlorophenyl)-(S,S)-l,2-propandiol(Preparation example 14), to obtain the title compound (1.91g, yield 20-50%).

1H NMR(400MHz, CDC1 ₃ ) δ 1.10 (d, J=6.8Hz, 3H), 2.42(m, 1H), 3.12(d, J=5Hz, 1H), 4.37(d, J=6Hz, 2H), 5.12~5.19(m, 3H), 7.05~7.66(m, 9H)

Preparation Example 247 : Synthesis of l-(2-chlorophenyl)-(S)-l-hydroxy-3- methyl-butyl-(S)-2-bicyclo[2,2,l]heptanescarbamate

The substantially same method as described in Example 123 was conducted, except that l-(2-iodophenyl)-(S,S)-l,2-butanediol(Preparation example 68) was used instead of l-(2- chlorophenyl)-(S,S)-l,2-propandiol(Preparation example 14), to obtain the title compound (1.68g, yield 20-50%).

1H NM (400MHz, CDC1 ₃ ) 61.01(d, J=6.8Hz, 6H), 1.08~1.35(m, 6H), 1.55~1.62(m, 2H), 1.65(br s, 1H), 1.75~1.71(m, 1H), 2.14~2.24(m, 1H), 2.42(m, 1H), 2.27~2.30(m, 1H), 3.23~3.29(m, 1H), 3.47~3.52(m, 1H), 4.67(br s, 1H), 5.01~5.09(m, 1H), 5.12~5.18(m, 1H), 7.02~7.65(m, 4H)

Preparation Example 248: Synthesis of l-(2-iodophenyl)-(S)-l-hydroxyhexyl-(S)-2- methylcarbamate

The substantially same method as described in Example 117 was conducted, except that l-(2-iodophenyl)-(S,S)-l,2-hexanediol(Preparation example 85) was used instead of l-(2- iodophenyl)-(S,S)-l,2-propandiol(Preparation example 66), to obtain the title compound (1.58g, yield 20-50%).

1H NMR(400MHz, CDC1 ₃ ) 60.97(t, J=6.4Hz, 3H), 1.29-1.33(m, 4H), 1.53(m, 2H), 2.76(s, 3H), 3.34(s, 1H), 4.80(br s 1H), 5.04(t, J=12.5Hz, 1H), 5.14(s, 1H), 7.01~7.63(m, 4H)

Preparation Example 249 : Synthesis of l-(2-iodophenyl)-(S)-l-hydroxyhexyl-(S)-2- propylcarbamate

The substantially same method as described in Example 118 was conducted, except that l-(2-iodophenyl)-(S,S)-l ,2-hexanediol(Preparation example 85) was used instead of l-(2- iodophenyl)-(S,S)-l,2-propandiol(Preparation example 66), to obtain the title compound (1.38g, yield 20-50%).

Ή NMR(400MHz, CDC1 ₃ ) 50.96(t, J=6.8Hz, 3H), 0.97(t, J=6.4Hz, 3H), 1.29~1.33(m, 4H), 1.53(m, 2H), 1.55~1.60(m, 2H), 2.96(t, J= 6.0, 2H), 3.34(s, 1H), 4.84(br s, 1H), 5.05(t, J=5.88Hz, 1H), 5.14(s, 1H), 7.02~7.63(m, 4H)

Preparation Example 250: Synthesis of l-(2-iodophenyl)-(S)-l-hydroxyhexyl-(S)-2- isopropylcarbamate

The substantially same method as described in Example 119 was conducted, except that l-(2-iodophenyl)-(S,S)-l,2-hexanediol(Preparation example 85) was used instead of l-(2- chlorophenyl)-(S,S)-l,2-propandiol(Preparation example 14), to obtain the title compound (1.73g, yield 20-50%).

1H NMR(400MHz, CDC1 ₃ ) 50.97(t, J=6.4Hz, 3H), 1.14(d, J=6.5Hz, 6H), 1.29~1.33(m, 4H), 1.53(m, 2H), 3.90~3.98(m, 1H), 3.73-3.82(m, 1H), 4.59(br s, 1H), 5.01-5.07(m, 1H), 5.14(t, J=5.8Hz, 1H), 7.01~7.65(m, 4H)

Preparation Example 251 : Synthesis of l-(2-iodophenyl)-(S)-l-hydroxyhexyl-(S)-2- cyclopropylcarbamate

The substantially same method as described in Example 120 was conducted, except that l-(2-iodophenyl)-(S,S)-l,2-hexanediol(Preparation example 85) was used instead of l-(2- chlorophenyl)-(S,S)-l,2-propandiol(Preparation example 14), to obtain the title compound (1.81g, yield 20-50%).

^J H NMR(400MHz, CDC1 ₃ ) 50.50~0.56(m, 2H), 0.74(d, J=7.21Hz, 2H), 0.97(t, J=6.4Hz, 3H), 1.29~1.33(m, 4H), 1.53(m, 2H), 2.38~2.44(m, 1H), 3.72(s, 1H), 4.98(br s, 1H), 5.05~5.11(m, 1H), 7.16(s, 1H), 6.96~7.57(m, 4H)

Preparation Example 252 : Synthesis of l-(2-iodophenyl)-(S)-l-hydroxyhexyl-(S)-2- cyclohexyl carbamate

The substantially same method as described in Example 121 was conducted, except that l-(2-iodophenyl)-(S,S)-l,2-hexanediol(Preparation example 85) was used instead of l-(2- chlorophenyl)-(S,S)-l,2-propandiol(Preparation example 14), to obtain the title compound (1.79g, yield 20-50%).

Ή NMR(400MHz, CDC1 ₃ ) 60.97(t, J=6.4Hz, 3H), l .l l~1.21(m, 4H), 1.29~1.33(m, 4H), 1.47~1.49(m, 4H), 1.53(m, 2H), 1.69~1.71(m, 2H), 3.19(d, J=4.32Hz, 1H), 3.45(s, 1H), 4.64(br s 1H), 5.02~5.07(m, 1H), 5.14(t, J=6.08Hz, 1H) 7.02~7.63(m, 4H)

Preparation Example 253 : Synthesis of l-(2-iodophenyl)-(S)-l-hydroxyhexyl-(S)-2- benzyl carbamate

The substantially same method as described in Example 122 was conducted, except that l-(2-iodophenyl)-(S,S)-l,2-hexanediol(Preparation example 85) was used instead of l-(2- chlorophenyl)-(S,S)-l,2-propandiol(Preparation example 14), to obtain the title compound (1.51g, yield 20-50%).

1H NMR(400MHz, CDC1 ₃ ) 50.97(t, J=6.4Hz, 3H), 1.29~1.33(m, 4H), 1.53(m, 2H), 3.12(d, J=5Hz, 1H), 4.37(d, J=6Hz, 2H), 5.12~5.19(m, 3H), 7.05~7.66(m, 9H)

Preparation Example 254 : Synthesis of l-(2-chIorophenyI)-(S)-l-hydroxyhexyl-(S)- 2-bicyclo[2,2,l]heptanescarbamate

The substantially same method as described in Example 123 was conducted, except that l-(2-iodophenyl)-(S,S)-l,2-butanediol(Preparation example 68) was used instead of l-(2- chlorophenyl)-(S,S)-l ,2-propandiol(Preparation example 14), to obtain the title compound (1.68g, yield 20-50%).

1H NMR(400MHz, CDC1 ₃ ) 60.97(t, J=6.4Hz, 3H), 1.08~1.35(m, 6H), 1.29~1.33(m, 4H), 1.53(m, 2H), 1.55~1.62(m, 2H), 1.65(br s, 1H), 1.75~1.71(m, 1H), 2.14~2.24(m, 1H), 2.27~2.30(m, 1H), 3.23~3.29(m, 1H), 3.47~3.52(m, 1H), 4.67(br s, 1H), 5.01~5.09(m, 1H), 5.12~5.18(m, 1H), 7.02~7.65(m, 4H)

Preparation Example 255 : Synthesis of l-(3-iodophenyl)-(S)-l-hydroxypropyl-(S)- 2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(3-iodophenyl)-(S,S)-l ,2-butanediol obtained in Preparation Example 87 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (2.04g, yield 30-60%).

1H NMR(400MHz, CDC1 ₃ ) 60.96(t. J=7.4Hz, 3H), 1.53~1.73(m, 2H), 3.09(br s, 1H), 4.83(br s, 2H), 5.00-5.10(m, 2H), 6.96-7.57(m, 4H)

Preparation Example 256 : Synthesis of l-(3-iodophenyl)-(S)-l-hydroxybutyl-(S)-2- carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(3-iodophenyl)-(S,S)-l,2-butanediol obtained in Preparation Example 89 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (1.49g, yield 30-60%).

1H NMR(400MHz, CDC1 ₃ ) 60.96(t. J=7.4Hz, 3H), 1.53~1.73(m, 2H), 3.09(br s, 1H), 4.83(br s, 2H), 5.00-5.10(m, 2H), 6.92-7.5 l(m, 4H)

Preparation Example 257 : Synthesis of l-(3-iodophenyl)-(S)-l-hydroxy-3-methyl- butyl-(S)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(3-iodophenyl)-3-methyl-(S,S)-l,2-butanediol obtained in Preparation Example 91 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (1.82g, yield 30-60%).

1H NMR(400MHz, CDC1 ₃ ) δ 5l .00(t, J = 7.2Hz, 6H), 1.73~1.79(m, 1H), 3.67~3.69(m, 1H), 4.85(br s, 2H), 5.40~5.43(m, 1H), 5.49~5.54(m, 1H), 6.97-7.53(m, 4H)

Preparation Example 258 : Synthesis of l-(3-iodophenyl)-(S)-l-hydroxyhexyyl-(S)- 2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(3-iodophenyl)-(S,S)-l,2-hexanediol obtained in Preparation Example 93 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (1.92g, yield 30-60%).

1H NMR(400MHz, CDC1 ₃ ) 50.84(t, J = 7.0Hz, 3H), 1.20~1.35(m, 4H), 1.36~1.41(m,

1H), 1.59~1.63(m, 1H), 3.71(d, J= 10.0Hz, 1H), 4.74(br s, 2H), 5.40~5.44(m, 1H), 5.52~5.57(m, lH), 7.01~7.55(m, 4H)

Preparation Example 259 : Synthesis of l-(4-fiuorophenyl)-(S)-l-hydroxypropyl- (S)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(4-fluorophenyl)-(S,S)-l,2-propanediol obtained in Preparation Example 95 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (1.61g, yield 30-60%).

1H NMR(400MHz, CDC1 ₃ ) 51.27(d, J=6.4Hz, 3H), 3.09(br s, 1H), 4.83(br s, 2H), 5.00-5.10(m, 2H), 6.89~7.05(m, 4H)

Preparation Example 260 : Synthesis of l-(4-fluorophenyl)-(S)-l-hydroxybutyl-(S)- 2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(4-fluorophenyl)-(S,S)-l,2-butanediol obtained in Preparation Example 97 was used instead of l-(2-chlorophenyl)-(S,S)-l ,2-propanediol, to obtain the title compound (1.55g, yield 30-60%).

1H N R(400MHz, CDC1 ₃ ) 80.96(t. J=7.4Hz, 3H), 1.53-1.73(m, 2H), 3.09(br s, 1H), 4.83(br s, 2H), 5.00~5.10(m, 2H), 6.92~7.09(m, 4H)

Preparation Example 261 : Synthesis of l-(4-fluorophenyi)-(S)-l-hydroxy-3-methyl- butyl-(S -2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(4-fluorophenyl)-3-methyl-(S,S)-l,2-butanediol obtained in Preparation Example 99 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (1.97g, yield 30-60%).

1H NMR(400MHz, CDC1 ₃ ) δ 6l.00(t, J = 7.2Hz, 6H), 1.73~1.79(m, 1H), 3.67~3.69(m, 1H), 4.85(br s, 2H), 5.40~5.43(m, 1H), 5.49~5.54(m, 1H), 6.94~7.03(m, 4H)

Preparation Example 262 : Synthesis of l-(4-fluorophenyl)-(S)-l-hydroxyhexyyl- (S)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(4-fluorophenyl)-(S,S)-l,2-hexanediol obtained in Preparation Example 101 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (1.86g, yield 30-60%).

1H NMR(400MHz, CDCI ₃ ) 50.84(t, J = 7.0Hz, 3H), 1.20~1.35(m, 4H), 1.36~1.41(m,

1H), 1.59~1.63(m, 1H), 3.71(d, J= 10.0Hz, 1H), 4.74(br s, 2H), 5.40~5.44(m, 1H), 5.52~5.57(m, 1H), 6.95-7.17(m, 4H)

Preparation Example 263 : Synthesis of l-(2-iodophenyl)-(R)-l-hydroxybutyl-(R)- 2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2-iodophenyl)-(R,R)-l,2-butanediol obtained in Preparation Example 69 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (1.98g, yield 30-60%).

1H NMR(400MHz, CDC1 ₃ ) 81.27(d, J=6.4Hz, 3H), 3.09(br s, 1H), 4.83(br s, 2H), 5.00~5.10(m, 2H), 7.00~7.76(m, 4H)

Preparation Example 264 : Synthesis of l-(2-iodophenyl)-(R)-l-hydroxy-3-methyl- butyl-( -2-carbamate

The substantially same method as described in Example 169 was conducted, except that l-(2-iodophenyl)-3-methyl-(R,R)-l,2-butanediol(Preparation example 84) was used instead of 1 - (2-iodophenyl)-(S,S)-l,2-butanediol(Preparation Example 68), to obtain the title compound (1.88g, yield 20-50%).

1H NMR(400MHz, CDC1 ₃ ) 60.97(d, J=6.4Hz, 6H), 2.36~2.52(m, 1H), 3.34(s, 1H), 4.80(br s 2H), 5.04(t, J=12.5Hz, 1H), 5.14(s, 1H), 7.01~7.63(m, 4H)

Preparation Example 265 : Synthesis of l-(2-iodophenyl)-(R)-l-hydroxyhexyl-(R)- 2-carba

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2-iodophenyl)-(R,R)-l,2-hexanediol obtained in Preparation Example 86 was used instead of l-(2-chlorophenyl)-(S,S)-l ,2-propanediol, to obtain the title compound (1.68g, yield 30-60%).

Ή NMR(400MHz, CDC1 ₃ ) 50.84(t, J = 7.0Hz, 3H), 1.20~1.35(m, 4H), 1.36~1.41(m,

1H), 1.59~1.63(m, 1H), 3.71(d, J= 10.0Hz, 1H), 4.74(br s, 2H), 5.40~5.44(m, 1H), 5.52~5.57(m, 1H), 6.99~7.55(m, 4H)

Preparation Example 266 : Synthesis of l-(4-fluorophenyl)-(R)-l-hydroxypropyl- (R)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(4-fluorophenyl)-(R,R)-l,2-propanediol obtained in Preparation Example 96 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (1.49g, yield 30-60%).

Ή NMR(400MHz, CDC1 ₃ ) 61.27(d, J=6.4Hz, 3H), 3.09(br s, 1H), 4.83(br s, 2H), 5.00-5.10(m, 2H), 7.00~7.22(m, 4H)

Preparation Example 267 : Synthesis of l-(4-fluorophenyl)-(R)-l-hydroxybutyl-(R)- 2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(4-fluorophenyl)-(R,R)-l,2-butanediol obtained in Preparation Example 98 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (2.25g, yield 30-60%).

Ή NMR(400MHz, CDC1 ₃ ) 60.96(t. J=7.4Hz, 3H), 1.53~1.73(m, 2H), 3.09(br s, 1H), 4.83(br s, 2H), 5.00-5.10(m, 2H), 6.92~7.20(m, 4H) Preparation Example 268 : Synthesis of l-(4-fluorophenyI)-(R)-l-hydroxy-3- methyl-butyl-(R)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(4-fluorophenyl)-3-methyl-(R,R)-l,2-butanediol obtained in Preparation Example 100 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (1.74g, yield 30-60%).

1H NMR(400MHz, CDC1 ₃ ) δ 5l.00(t, J = 7.2Hz, 6H), 1.73~1.79(m, 1H), 3.67~3.69(m, 1H), 4.85(br s, 2H), 5.40~5.43(m, 1H), 5.49~5.54(m, 1H), 6.92~7.20(m, 4H)

Preparation Example 269 : Synthesis of l-(4-fluorophenyl)-(R)-l-hydroxyhexyyl- (R)-2-carb amate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(4-fluorophenyl)-(R,R)-l,2-hexanediol obtained in Preparation Example 102 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (1.59g, yield 30-60%).

1H NMR(400MHz, CDC1 ₃ ) 50.84(t, J = 7.0Hz, 3H), 1.20~1.35(m, 4H), 1.36~1.41(m,

1H), 1.59~1.63(m, 1H), 3.71(d, J= 10.0Hz, 1H), 4.74(br s, 2H), 5.40~5.44(m, 1H), 5.52~5.57(m, 1H), 6.95-7.2 l(m, 4H)

Preparation Example 270 : Synthesis of l-(3-iodophenyI)-(R)-l-hydroxypropyl-(R)- 2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(3-iodophenyl)-(R,R)-l,2-butanediol obtained in Preparation Example 88 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (1.54g, yield 30-60%).

1H NMR(400MHz, CDC1 ₃ ) 60.96(t. J=7.4Hz, 3H), 1.53~1.73(m, 2H), 3.09(br s, 1H), 4.83(br s, 2H), 5.00-5.10(m, 2H), 6.96~7.57(m, 4H)

Preparation Example 271 : Synthesis of l-(3-iodophenyI)-(R)-l-hydroxybutyl-(R)- 2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(3-iodophenyl)-(R,R)-l,2-butanediol obtained in Preparation Example 90 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (1.44g, yield 30-60%).

^] H NMR(400MHz, CDC1 ₃ ) 60.96(t. J=7.4Hz, 3H), 1.53~1.73(m, 2H), 3.09(br s, 1H), 4.83(br s, 2H), 5.00-5.10(m, 2H), 6.92-7.5 l(m, 4H)

Preparation Example 272 : Synthesis of l-(3-iodophenyl)-(R)-l-hydroxy-3-methyl- butyl-(R)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(3-iodophenyl)-3-methyl-(R,R)-l,2-butanediol obtained in Preparation Example 92 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (1.65g, yield 30-60%).

1H NMR(400MHz, CDC1 ₃ ) δ 5l.00(t, J = 7.2Hz, 6H), 1.73~1.79(m, 1H), 3.67~3.69(m,

1H), 4.85(br s, 2H), 5.40~5.43(m, 1H), 5.49~5.54(m, 1H), 6.97~7.53(m, 4H)

Preparation Example 273 : Synthesis of l-(3-iodophenyl)-(R)-l-hydroxyhexyyl-(R)- 2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(3-iodophenyl)-(R,R)-l,2-hexanediol obtained in Preparation Example 94 was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (1.71g, yield 30-60%).

1H NMR(400MHz, CDC1 ₃ ) 50.84(t, J=7.0Hz, 3H), 1.20~1.35(m, 4H), 1.36~1.41(m, 1H),

1.59~1.63(m, 1H), 3.71(d, J=10.0Hz, 1H), 4.74(br s, 2H), 5.40~5.44(m, 1H), 5.52~5.57(m, 1H), 7.01~7.55(m, 4H)

Preparation Example 274: Synthesis of l-(2,6-difluorophenyi)-trans-l-propene

The substantially same method as described in Preparation Example 1 was conducted, except that 2,6-difluorobenzenaldehyde was used instead of 2-chlorobenzenaldehyde, to obtain the title compound (3.4g, yield 52%).

1H NMR(400MHz, CDC1 ₃ ) 51.95(dd, J=6.8Hz, 1.6Hz, 3H), 6.24(m, 1H), 6.72(d, J=15.6Hz, 1H), 7.18~7.44(m, 3H)

Preparation Example 275: Synthesis of l-(2,6-difluorophenyl)-(S,S)-l,2- propanediol

The substantially same method as described in Preparation Example 14 was conducted, except that l-(2,6-difluorophenyl)-trans-l-propene(Preparation Example 275) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (1.5g, yield 60-90%).

1H NMR(400MHz, CDC1 ₃ ) 61.10(d, J-6.4Hz, 3H), 2.72(d, J=2.4Hz, 1H), 3.10(d, J=8.4Hz, 1H), 4.47~4.54(m, 1H), 5.24(t, J=8.8Hz, 1H), 7.18~7.36(m, 3H)

Preparation Example 276 : Synthesis of l-(2,6-difluorophenyl)-(S)-l- hydroxypropyl-(S)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,6-difluorophenyl)-l,2-propanediol( Preparation Example 275) was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (2.4g, yield 20~60%).

1H NMR(400MHz, CDC1 ₃ ) 5l.l5(d, J = 6.4Hz, 3H), 3.66(d, J = 9.2Hz, 1H), 4.73(br s,

2H), 5.43(t, J= 9.0Hz, 1H), 5.62~5.69(m, 1H), 7.18~7.22(m, 3H),

Preparation Example 277: Synthesis of l-(2,5-dichlorophenyl)-trans-l-propene

The substantially same method as described in Preparation Example 1 was conducted, except that 2,5-dichlorobenzenaldehyde was used instead of 2-chlorobenzenaldehyde, to obtain the title compound (3.1 g, yield 52%).

Ή NMR(400MHz, CDC1 ₃ ) 61.95(dd, J=6.8Hz, 1.6Hz, 3H), 6.24(m, 1H), 6.72(d, J=l 5.6Hz, 1H), 7.09~7.25(m, 3H)

Preparation Example 278: Synthesis of l-(2,5-dichlorophenyl)-(S,S)-l,2- propanediol

The substantially same method as described in Preparation Example 14 was conducted, except that l-(2,5-dichlorophenyl)-trans-l-propene(Preparation Example 277) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (1.9g, yield 60-90%).

1H NMR(400MHz, CDC1 ₃ ) 61.10(d, J=6.4Hz, 3H), 2.72(d, J=2.4Hz, 1H), 3.10(d, J=8.4Hz, 1H), 4.47~4.54(m, 1H), 5.24(t, J=8.8Hz, 1H), 7..14~7.26(m, 3H)

Preparation Example 279 : Synthesis of l-(2,5-dichlorophenyl)-l-hydroxypropyl-2- carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,5-dichlorophenyl)-l,2-propanediol(Preparation Example 278) was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (2.29g, yield 20~60%).

1H NMR(400MHz, CDC1 ₃ ) 6l.l5(d, J = 6.4Hz, 3H), 3.66(d, J=9.2Hz, 1H), 4.73(br s, 2H), 5.43(t, J= 9.0Hz, 1H), 5.62~5.69(m, 1H), 7.18~7.22(m, 3H)

Preparation Example 280: Synthesis of l-(2,5-dichlorophenyl)-(R,R)-l,2- propanediol

The substantially same method as described in Preparation Example 15 was conducted, except that l-(2,5-dichlorophenyl)-trans-l-propene(Preparation Example 277) was used instead of l-(2-chlorophenyl)-trans-l-propene(Preparation Example 1), to obtain the title compound (2.3g, yield 60-90%).

1H NMR(400MHz, CDC1 ₃ ) 61.10(d, J=6.4Hz, 3H), 2.72(d, J=2.4Hz, 1H), 3.10(d, J=8.4Hz, 1H), 4.47~4.54(m, 1H), 5.24(t, J=8.8Hz, 1H), 7.14~7.26(m, 3H)

Preparation Example 281 : Synthesis of l-(2,5-dichlorophenyI)-(R)-l- hydroxypropyl-(R)-2-carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2,5-dichlorophenyl)-l,2-propanediol(Preparation Example 278) was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (2.25g, yield 20-60%).

1H NMR(400MHz, CDC1 ₃ ) 5l.l5(d, J = 6.4Hz, 3H), 3.66(d, J=9.2Hz, 1H), 4.73(br s, 2H), 5.43(t, J = 9.0Hz, 1H), 5.62-5.69(m, 1H), 7.13~7.25(m, 3H)

Preparation Example 282 : Synthesis of l-(2-chlorophenyl)-l-(S)-l,2-ethanediol

The substantially same method as described in Preparation Example 14 was conducted, except that 2-chlorostyrene(Aldrich No.160679) was used instead of l-(2-chlorophenyl)-trans-l- propene(Preparation Example 1), to obtain the title compound (2.29g, yield 60-90%).

1H NMR(400MHz, CDC1 ₃ ) δ 2.72(d, J=2.4Hz, 1H), 3.10(d, J=8.4Hz, 1H), 4.47~4.54(m, 1H), 4.9 l(t, J=8.8Hz, 1H), 7.09~7.26(m, 4H) Preparation Example 283 : Synthesis of l-(2-chlorophenyl)-(S)-l-hydroxyethyl-2- carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that 1 -(2-chlorophenyl)- l-(S)-l,2-ethanediol(Preparation Example 282) was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (1.92g, yield 20-60%).

1H NMR(400MHz, CDC1 ₃ ) δ 1.72(br s, 1H), 4.26(dd, J=12.0, 7.8Hz, 1H), 4.39(dd,

J=12.0, 2.7Hz, 1H), 4.41(dd, J=7.8, 2.7Hz, 1H), 4.77(br 2H), 7.26~7.68(m, 4H)

Preparation Example 284 : Synthesis of 2-iodostyrene

The substantially same method as described in Preparation Example 64 was conducted, except that 2-propanone was used instead of 3-pentanone, to obtain the title compound (2.1g, yield 20-40%).

1H NMR(400MHz, CDC1 ₃ ) 55.34(dd, J=10.8, 0.8Hz, 1H), 5.65(dd, J=17.2, 0.8Hz, 6.89~7.92(m, 5H)

Preparation Example 285 : Synthesis of l-(2-iodophenyl)-l-(S)-l,2-ethanediol

The substantially same method as described in Preparation Example 14 was conducted, except that 2-iodostyrene(Preparation Example 284) was used instead of 1 -(2-chlorophenyl)- trans-l-propene(Preparation Example 1), to obtain the title compound (2.52g, yield 60-90%).

1H NMR(400MHz, CDC1 ₃ ) δ 2.07~2.13(m, 1H), 3.52~3.58(m, 1H), 3.89~3.94(m, 1H), 5.04-5.08(m, 1H), 7.01~7.85(m, 4H) Preparation Example 286 : Synthesis of l-(2-iodophenyl)-(S)-l-hydroxyethyl-2- carbamate

The substantially same method as described in Preparation Example 103 was conducted, except that 1 -(2-chlorophenyl)- l-(S)-l,2-ethanediol(Preparation Example 282) was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (1.92g, yield 20-60%).

1H NMR(400MHz, CDC1 ₃ ) δ 1.72(br s, 1H), 4.26(dd, J=12.0, 7.8Hz, 1H), 4.39(dd, J=12.0, 2.7Hz, 1H), 4.41(dd, J=7.8, 2.7Hz, 1H), 4.77(br 2H), 7.06~7.29(m, 4H)

Preparation Example 287 : Synthesis of 2-fluorostyrene

The substantially same method as described in Preparation Example 284 was conducted, except that 2-fluorobenzaldehyde(Aldrich No. F4807) was used instead of 2- iodobenzaldehyde(Praparation Example 63) to obtain the title compound (1.82g, yield 20-40%).

1H NMPv(400MHz, CDC1 ₃ ) 65.34(dd, J=10.8, 0.8Hz, 1H), 5.65(dd, J=17.2, 0.8Hz, 1H), 6.92~7.89(m, 5H)

Preparation Example 285 : Synthesis of l-(2-fluorophenyl)-l-(S)-l,2-ethanediol

The substantially same method as described in Preparation Example 14 was conducted, except that 2-fluorostyrene(Preparation Example 287) was used instead of 1 -(2-chlorophenyl)- trans-l-propene(Preparation Example 1), to obtain the title compound (2.32g, yield 60-90%).

1H NMR(400MHz, CDC1 ₃ ) δ 2.07~2.13(m, 1H), 3.52~3.58(m, 1H), 3.89~3.94(m, 1H), 5.04~5.08(m, 1H), 6.90~7.17(m, 4H)

Preparation Example 286 : Synthesis of l-(2-fluorophenyl)-(S)-l-hydroxyethyl-2- carb

The substantially same method as described in Preparation Example 103 was conducted, except that l-(2-fluorophenyl)-l-(S)-l,2-ethanediol(Preparation Example 285) was used instead of l-(2-chlorophenyl)-(S,S)-l,2-propanediol, to obtain the title compound (1.59g, yield 20-60%).

1H NMR(400MHz, CDC1 ₃ ) δ 1.72(br s, 1H), 4.26(dd, J=12.0, 7.8Hz, 1H), 4.39(dd, J=12.0, 2.7Hz, 1H), 4.41(dd, J=7.8, 2.7Hz, 1H), 4.77(br 2H), 7.01~7.27(m, 4H)

Example scheme I : Synthesis of l-(n-halophenyl)-l-methoxymethoxyalkyl-2- alkylcarbamate (Examples 1 to 123, 271 to 274 and 276 to 278)

To a stirred solution of l-(n-halophenyl)-l-hydorxyalkyl-2-alkylcarbamate in MC( ethylenechloloride) was added DIPEA(Diisopropylethylamine) at 0 °C under N ₂ condition. The mixture was added MOM-Cl(MO chloride) at 0 ^° C then slowly warm to R.T. When the reaction was completed, the obtained product was washed with H ₂ 0 and MC. The separated organic layer was dehydrated with anhydrous MgSC>4(Magnesium sulfate), filtrated, and concented under reduced pressure. The concentrated residue was purified by a silicagel aolumn chromatography, to obtain title compound(Yield 40-60%)

Example scheme II : Synthesis of l-(n-halophenyl)-l-methoxyalkyl-2- alkylcarbamate (Examples 124 to 246, 275 and 279 to 281)

1 -(n-halophenyl)- 1 -hydorxyalkyl-2-alkylcarbamate, THF(Tetrahydrofuran), Mel(Methyliodide) and t-BuOH(Potassium tert-butoxide) were put into a flask and stirred at the 0 ^° C. When the reaction was completed, the obtained product was washed with 1M HCl solution and EA(Ethylacetate). The separated organic layer was dehydrated with anhydrous MgS04(Magnesium sulfate), filtrated, and concented under reduced pressure. The concentrated residue was purified by a silicagel aolumn chromatography, to obtain title compound(Yield 20-40%)

Example scheme III : Synthesis of l-(n-halophenyl)-l-carbamoyloxyalkyI-2- alkylcarbamate (Examples 247 to 270)

1 -(n-halophenyl)- 1-hydroxypropyl-l -carbamate, tetrahydrofuran (THF), and carbonyldiimidazole (CDI) were put into a flask and stirred at the room temperature. After approximately 3 hours, ammonia solution (NH ₄ OH) was added thereto. When the reaction was completed, the obtained product was washed with 1M HCl solution and ethylacetate (EA). The separated organic layer was dehydrated with anhydrous MgS0 ₄ (Magnesium sulfate), filtrated, and concented under reduced pressure. The concentrated residue was purified by a silica gel column chromatography, to obtain the title compound (yield 75~95%). According to the above described methods, the compounds as defined in following Tables 1 and 2 were prepared.

(Table 1) Carbamate derivetives (B is not a carbamoyl derivative)

I 2 Carbamoyl MOM Et Benzyl S S

I 2 Carbamoyl MOM Et Bicycloheptyl S S

I 2 Carbamoyl MOM Isopropyl H s s

I 2 Carbamoyl MOM Isopropyl Me s s

I 2 Carbamoyl MOM Isopropyl Propyl s s

I 2 Carbamoyl MOM Isopropyl Isopropyl s s

I 2 Carbamoyl MOM Isopropyl Cyclopropyl s s

I 2 Carbamoyl MOM Isopropyl Cyclohexyl s s

I 2 Carbamoyl MOM Isopropyl Benzyl s s

I 2 Carbamoyl MOM Isopropyl Bicycloheptyl s s

I 2 Carbamoyl MOM Butyl H s s

I 2 Carbamoyl MOM Butyl Me s s

I 2 Carbamoyl MOM Butyl Propyl s s

I 2 Carbamoyl MOM Butyl Isopropyl s s

I 2 Carbamoyl MOM Butyl Cuclopropyl s s

I 2 Carbamoyl MOM Butyl Cyclohexyl s s

I 2 Carbamoyl MOM Butyl Benzyl s s

I 2 Carbamoyl MOM Butyl Bicycloheptyl s s

I 3 Carbamoyl MOM Me H s s

I 3 Carbamoyl MOM Et H s s

I 3 Carbamoyl MOM Isopropyl H s s ^' I 3 Carbamoyl MOM Butyl H s s

F 4 Carbamoyl MOM Me H s s

F 4 Carbamoyl MOM Et H s s

F 4 Carbamoyl MOM Isopropyl H s s

F 4 Carbamoyl MOM Butyl H s s

CI 2,4 Carbamoyl MOM Me H s s

CI 2,4 Carbamoyl MOM Et H s s

CI 2,4 Carbamoyl MOM Isopropyl H s s

CI 2,4 Carbamoyl MOM Butyl H s s

CI 2,6 Carbamoyl MOM Me H s s

CI 2,6 Carbamoyl MOM Et H s s

CI 2,6 Carbamoyl MOM Isopropyl H s s

CI 2,6 Carbamoyl MOM Butyl H s s

CI 2,3 Carbamoyl MOM Me H s s

CI 2 Carbamoyl MOM Me H R R

CI 2 Carbamoyl MOM Me H rac rac

CI 2 Carbamoyl MOM Me H R S 72 CI 2 Carbamoyl MOM Me H S R

73 CI 2 Carbamoyl MOM Et H R R

74 CI 2 Carbamoyl MOM Et H rac rac

75 CI 2 Carbamoyl MOM Isopropyl H R R

76 CI 2 Carbamoyl MOM Isopropyl H rac rac

77 CI 2 Carbamoyl MOM Butyl H R R

78 CI 2 Carbamoyl MOM Butyl H rac rac

79 CI 2 Carbamoyl MOM Me Me R R

80 CI 2 Carbamoyl MOM Me Propyl R R

81 CI 2 Carbamoyl MOM Me Isopropyl R R

82 CI 2 Carbamoyl MOM Me Cyclopropyl R R

83 CI 2 Carbamoyl MOM Me Cyclohexyl R R

84 CI 2 Carbamoyl MOM Me Benzyl R R

85 CI 2 Carbamoyl MOM Me Bicycloheptyl R R

86 F 2 Carbamoyl MOM Me H R R

87 F 4 Carbamoyl MOM Me H R R

88 F 4 Carbamoyl MOM Et H R R

89 F 4 Carbamoyl MOM Isopropyl H R R

90 F 4 Carbamoyl MOM Butyl H R R

91 I 2 Carbamoyl MOM Me H R R

92 I 2 Carbamoyl MOM Et H R R

93 I 2 Carbamoyl MOM Isopropyl H R R

94 I 2 Carbamoyl MOM Butyl H R R

95 I 3 Carbamoyl MOM Me H R R

96 I 3 Carbamoyl MOM Et H R R

97 I 3 Carbamoyl MOM Isopropyl H R R

98 I 3 Carbamoyl MOM Butyl H R R

99 CI 2 Carbamoyl MOM Me Me rac rac

100 CI 2 Carbamoyl MOM Me Propyl rac rac

101 CI 2 Carbamoyl MOM Me Isopropyl rac rac

102 CI 2 Carbamoyl MOM Me Cyclopropyl rac rac

103 CI 2 Carbamoyl MOM Me Cyclohexyl rac rac

104 CI 2 Carbamoyl MOM Me Benzyl rac rac

105 CI 2 Carbamoyl MOM Me Bicycloheptyl rac rac

106 CI 2,4 Carbamoyl MOM Me H R R

107 CI 2,6 Carbamoyl MOM Me H R R

108 CI 2,3 Carbamoyl MOM Me H R R

109 CI 2,4 Carbamoyl MOM Et H R R 110 CI 2,6 Carbamoyl MOM Et H R R

111 CI 2,4 Carbamoyl MOM Isopropyl H R R

112 CI 2,6 Carbamoyl MOM Isopropyl H R R

1 13 CI 2,4 Carbamoyl MOM Butyl H R R

114 CI 2,6 Carbamoyl MOM Butyl H R R

1 15 CI 2,4 Carbamoyl MOM Me H rac rac

1 16 CI 2,6 Carbamoyl MOM Me H rac rac

117 CI 2,3 Carbamoyl MOM Me H rac rac

118 CI 2,4 Carbamoyl MOM Et H rac rac

119 CI 2,6 Carbamoyl MOM Et H rac rac

120 CI 2,4 Carbamoyl MOM Isopropyl H rac rac

121 CI 2,6 Carbamoyl MOM Isopropyl H rac rac

122 CI 2,4 Carbamoyl MOM Butyl H rac rac

123 CI 2,6 Carbamoyl MOM Butyl H rac rac

124 CI 2 Carbamoyl Methyl Me H S S

125 CI 2 Carbamoyl Methyl Me Me S S

126 CI 2 Carbamoyl Methyl Me Propyl S S

127 CI 2 Carbamoyl Methyl Me Isopropyl S S

128 CI 2 Carbamoyl Methyl Me Cuclopropyl S S

129 CI 2 Carbamoyl Methyl Me Cyclohexyl S S

130 CI 2 Carbamoyl Methyl Me Benzyl S S

131 CI 2 Carbamoyl Methyl Me Bicycloheptyl s S 32 CI 2 Carbamoyl Methyl Et H s S 33 CI 2 Carbamoyl Methyl Isopropyl H s S 34 CI 2 Carbamoyl Methyl Butyl H s S 35 F 2 Carbamoyl Methyl Me H s S 36 F 2 Carbamoyl Methyl Me Me s s 37 F 2 Carbamoyl Methyl Me Propyl s s 38 F 2 Carbamoyl Methyl Me Isopropyl s s 39 F 2 Carbamoyl Methyl Me Cuclopropyl s s40 F 2 Carbamoyl Methyl Me Cyclohexyl s s 41 F 2 Carbamoyl Methyl Me Benzyl s s42 F 2 Carbamoyl Methyl Me Bicycloheptyl s s43 I 2 Carbamoyl Methyl Me H s s44 I 2 Carbamoyl Methyl Me Me s s45 I 2 Carbamoyl Methyl Me Propyl s s46 I 2 Carbamoyl Methyl Me Isopropyl s s47 I 2 Carbamoyl Methyl Me Cuclopropyl s s 148 I 2 Carbamoyl Methyl Me Cyclohexyl S s

149 I 2 Carbamoyl Methyl Me Benzyl S s

150 I 2 Carbamoyl Methyl Me Bicycloheptyl s s

151 I 2 Carbamoyl Methyl Et H s s

152 I 2 Carbamoyl Methyl Et Me s s

153 I 2 Carbamoyl Methyl Et Propyl s s

154 I 2 Carbamoyl Methyl Et Isopropyl s s

155 I 2 Carbamoyl Methyl Et Cyclopropyl s s

156 I 2 Carbamoyl Methyl Et Cyclohexyl s s

157 I 2 Carbamoyl Methyl Et Benzyl s s

158 I 2 Carbamoyl Methyl Et Bicycloheptyl s s

159 I 2 Carbamoyl Methyl Isopropyl H s s

160 I 2 Carbamoyl Methyl Isopropyl Me s s

161 I 2 Carbamoyl Methyl Isopropyl Propyl s s

162 I 2 Carbamoyl Methyl Isopropyl Isopropyl s s

163 I 2 Carbamoyl Methyl Isopropyl Cyclopropyl s s

164 I 2 Carbamoyl Methyl Isopropyl Cyclohexyl s s

165 I 2 Carbamoyl Methyl Isopropyl Benzyl s s

166 I 2 Carbamoyl Methyl Isopropyl Bicycloheptyl s s

167 I 2 Carbamoyl Methyl Butyl H s s

168 I 2 Carbamoyl Methyl Butyl Me s s

169 I 2 Carbamoyl Methyl Butyl Propyl s s

170 I 2 Carbamoyl Methyl Butyl Isopropyl s s

171 I 2 Carbamoyl Methyl Butyl Cuclopropyl s s

172 I 2 Carbamoyl Methyl Butyl Cyclohexyl s s

173 I 2 Carbamoyl Methyl Butyl Benzyl s s

174 I 2 Carbamoyl Methyl Butyl Bicycloheptyl s s

175 I 3 Carbamoyl Methyl Me H s s

176 I 3 Carbamoyl Methyl Et H s s

177 I 3 Carbamoyl Methyl Isopropyl H s s

178 I 3 Carbamoyl Methyl Butyl H s s

179 F 4 Carbamoyl Methyl Me H s s

180 F 4 Carbamoyl Methyl Et H s s

181 F 4 Carbamoyl Methyl Isopropyl H s s

182 F 4 Carbamoyl Methyl Butyl H s s

183 CI 2,4 Carbamoyl Methyl Me H s s

184 CI 2,4 Carbamoyl Methyl Et H s s

185 CI 2,4 Carbamoyl Methyl Isopropyl H s s 186 CI 2,4 Carbamoyl Methyl Butyl H S S

187 CI 2,6 Carbamoyl Methyl Me H S S

188 CI 2,6 Carbamoyl Methyl Et H S S

189 CI 2,6 Carbamoyl Methyl Isopropyl H S S

190 CI 2,6 Carbamoyl Methyl Butyl H S S

191 CI 2,3 Carbamoyl Methyl Me H S S

192 CI 2 Carbamoyl Methyl Me H R R

193 CI 2 Carbamoyl Methyl Me H rac rac

194 CI 2 Carbamoyl Methyl Me H R S

195 CI 2 Carbamoyl Methyl Me H S R

196 CI 2 Carbamoyl Methyl Et H R R

197 CI 2 Carbamoyl Methyl Et H rac rac

198 CI 2 Carbamoyl Methyl Isopropyl H R R

199 CI 2 Carbamoyl Methyl Isopropyl H rac rac

200 CI 2 Carbamoyl Methyl Butyl H R R

201 CI 2 Carbamoyl Methyl Butyl H rac rac

202 CI 2 . Carbamoyl Methyl Me Me R R

203 CI 2 Carbamoyl Methyl Me Propyl R R

204 CI 2 Carbamoyl Methyl Me Isopropyl R R

205 CI 2 Carbamoyl Methyl Me Cyclopropyl R R

206 CI 2 Carbamoyl Methyl Me Cyclohexyl R R

207 CI 2 Carbamoyl Methyl Me Benzyl R R

208 CI 2 Carbamoyl Methyl Me Bicycloheptyl R R

209 F 2 Carbamoyl Methyl Me H R R

210 F 4 Carbamoyl Methyl Me H R R

211 F 4 Carbamoyl Methyl Et H R R

212 F 4 Carbamoyl Methyl Isopropyl H R R

213 F 4 Carbamoyl Methyl Butyl H R R

214 I 2 Carbamoyl Methyl Me H R R

215 I 2 Carbamoyl Methyl Et H R R

216 I 2 Carbamoyl Methyl Isopropyl H R R

217 I 2 Carbamoyl Methyl Butyl H R R

218 I 3 Carbamoyl Methyl Me H R R

219 I 3 Carbamoyl Methyl Et H R R

220 I 3 Carbamoyl Methyl Isopropyl H R R

221 I 3 Carbamoyl Methyl Butyl H R R

222 CI 2 Carbamoyl Methyl Me Me rac rac

223 CI 2 Carbamoyl Methyl Me Propyl rac rac 224 CI 2 Carbamoyl Methyl Me Isopropyl rac rac

225 CI 2 Carbamoyl Methyl Me Cyclopropyl rac rac

226 CI 2 Carbamoyl Methyl Me Cyclohexyl rac rac

227 CI 2 Carbamoyl Methyl Me Benzyl rac rac

228 CI 2 Carbamoyl Methyl Me Bicycloheptyl rac rac

229 CI 2,4 Carbamoyl Methyl Me H R R

230 CI 2,6 Carbamoyl Methyl Me H R R

231 CI 2,3 Carbamoyl Methyl Me H R R

232 CI 2,4 Carbamoyl Methyl Et H R R

233 CI 2,6 Carbamoyl Methyl Et H R R

234 CI 2,4 Carbamoyl Methyl Isopropyl H R R

235 CI 2,6 Carbamoyl Methyl Isopropyl H R R

236 CI 2,4 Carbamoyl Methyl Butyl H R R

237 CI 2,6 Carbamoyl Methyl Butyl H R R

238 CI 2,4 Carbamoyl Methyl Me H rac rac

239 CI 2,6 Carbamoyl Methyl Me H rac rac

240 CI 2,3 Carbamoyl Methyl Me H rac rac

241 CI 2,4 Carbamoyl Methyl Et H rac rac

242 CI 2,6 Carbamoyl Methyl Et H rac rac

243 CI 2,4 Carbamoyl Methyl Isopropyl H rac rac

244 CI 2,6 Carbamoyl Methyl Isopropyl H rac rac

245 CI 2,4 Carbamoyl Methyl Butyl H rac rac

246 CI 2,6 Carbamoyl Methyl Butyl H rac rac

271 F 2,6 Carbamoyl MOM Me H S S

272 CI 2,5 Carbamoyl MOM Me H S S

273 CI 2,5 Carbamoyl MOM Me H R R

276 CI 2 Carbamoyl MOM H H S S

277 F 2 Carbamoyl MOM H H S s

278 I 2 Carbamoyl MOM H H s s

279 CI 2 Carbamoyl Methyl H H s s

280 F 2 Carbamoyl Methyl H H s s

281 I 2 Carbamoyl Methyl H H s s

(Table 2) Carbamate denvertives (B is a carbamoyl derivative) 249 CI 2 Carbamoyl Carbamoyl H Me Propyl S s

250 CI 2 Carbamoyl Carbamoyl H Me H R R

251 CI 2 Carbamoyl Carbamoyl H Me H rac rac

252 CI 2 Carbamoyl Carbamoyl H Et H S S

253 CI 2 Carbamoyl Carbamoyl H Isopropyl H S S

254 CI 2 Carbamoyl Carbamoyl H Butyl H S s

255 F 2 Carbamoyl Carbamoyl H Me H S s

256 F 2 Carbamoyl Carbamoyl H Et H S s

257 F 2 Carbamoyl Carbamoyl H Isopropyl H s s

258 F 2 Carbamoyl Carbamoyl H Butyl H s s

259 I 2 Carbamoyl Carbamoyl H Me H s s

260 I 2 Carbamoyl Carbamoyl H Et H s s

261 I 2 Carbamoyl Carbamoyl H Isopropyl H s s

262 I 2 Carbamoyl Carbamoyl H Butyl H s s

263 CI 2,4 . Carbamoyl Carbamoyl H Me H s s

264 CI 2,4 Carbamoyl Carbamoyl H Et H s s

265 CI 2,4 Carbamoyl Carbamoyl H Isopropyl H s s

266 CI 2,4 Carbamoyl Carbamoyl H Butyl H s s

267 CI 2,4 Carbamoyl Carbamoyl H Me H s s

268 CI 2,4 Carbamoyl Carbamoyl H Et H s s

269 CI 2,4 Carbamoyl Carbamoyl H Isopropyl H s s

270 CI 2,4 Carbamoyl Carbamoyl H Butyl H s s

274 CI 2 MOM Carbamoyl H Me H s s

275 CI 2 Methyl Carbamoyl H Me H s s

Example 1: Synthesis of l-(2-chlorophenyl)-(S)-l-methoxymethoxypropyl-(S)-2- carbamate

To a stirred solution of l-(2-chlorophenyl)-l-hydorxyalkyl-2-carbamate(Preparation Example 103, 1.7g) in MC(Methylenechloloride) was added DIPEA(Diisopropylethylamine, 5eq, 5.1ml) at 0°C under N ₂ condition. The mixture was added MOM-Cl(MOMchloride, 5eq, 2.3ml) at 0 ^° C then slowly warm to R.T. When the reaction was completed, the obtained product was washed with H ₂ 0 and MC. The separated organic layer was dehydrated with anhydrous MgS0 ₄ (Magnesium sulfate), filtrated, and concented under reduced pressure. The concentrated residue was purified by a silicagel aolumn chromatography, to obtain title compound.

1H NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8 Hz, 3H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.26~7.70(m, 4H)

According to the method described in Example 1, the following compounds of Examples 2 to 123 were prepared:

Example 2: Synthesis of l-(2-chlorophenyl)-(S)-l-methoxymethoxypropyl-(S)-2- methylcarbamate

Ή NMR(400MHz, CDC1 ₃ ) 51.37(d, J=6.8 Hz, 3H), 2.58(s, 3H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 3: Synthesis of l-(2-chlorophenyl)-(S)-l-methoxymethoxypropyl-(S)-2- propylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 60.90(t, J=6.8 Hz, 3H), 1.37(d, J=6.8 Hz, 3H), 1.60(m, 2H), 3.18(t, J=7.1Hz, 2H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 4: Synthesis of l-(2-chlorophenyl)-(S)-l-methoxymethoxypropyl-(S)-2- isopropylcarbamate

1H NMR(400MHz, CDC1 ₃ ) δ, 1.27(d, J=6.8 Hz, 6H), 1.37(d, J=6.8 Hz, 3H), 3.30(s, 3H), 4.17(m, 1H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 5: Synthesis of l-(2-chlorophenyl)-(S)-l-methoxymethoxypropyl-(S)-2- cyclopropylcarbamate

l NMR(400MHz, CDC1 ₃ ) 50.57(m, 2H), 0.82(m, 2H), 1.37(d, J=6.8 Hz, 3H), 2.75(m, 1H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 6: Synthesis of l-(2-chlorophenyl)-(S)-l-methoxymethoxypropyl-(S)-2- cyclohexylcarbamate

Ή NMR(400MHz, CDC1 ₃ ) 61.11-1.21 (m, 4H), 1.37(d, J=6.8 Hz, 3H), 1.47~1.49(m, 4H), 1.74(m, 2H), 3.30(s, 3H), 3.54(m, 1H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 7: Synthesis of l-(2-chlorophenyl)-(S)-l-methoxymethoxypropyl-(S)-2- cy clohexylcarb amate

^l NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8 Hz, 3H), 3.30(s, 3H), 4.20(m, 2H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.13~7.19(m, 4H), 7.37~7.88(m, 5H)

Example 8: Synthesis of l-(2-chlorophenyl)-(S)-l-methoxymethoxypropyl-(S)-2- bicyclo[2 2,l]neptanescarbamate

1H NMR(400MHz, CDC1 ₃ ) 61.33~1.58(m, 9H), 1.75~1.88(m, 2H), 2.06~2.13(m, 2H), 3.30(s, 3H), 3.53(m, 1H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.13~7.19(m, 4H), 7.37~7.88(m, 5H)

Example 9: Synthesis of l-(2-chlorophenyl)-(S)-l-methoxymethoxybutyl-(S)-2- carbam

lH NMR(400MHz, CDC1 ₃ ) 51.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 10: Synthesis of l-(2-chlorophenyl)-(S)-l-methoxymethoxy-3-methyl- butyl-(S -2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.07(t, J=7.6Hz, 6H), 1.83~1.89(m, 1H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 11: Synthesis of l-(2-chlorophenyl)-(S)-l-methoxymethoxyhexyl-(S)-2- carbamate

Ή NMR(400MHz, CDC1 ₃ ) 50.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 12: Synthesis of l-(2-fluorophenyl)-(S)-l-methoxymethoxypropyI-(S)-2- carbam

1H NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8 Hz, 3H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.15~7.68(m, 4H)

Example 13: Synthesis of l-(2-fiuorophenyl)-(S)-l-methoxymethoxypropyl-(S)-2- methylcarbamate

Ή NMR(400MHz, CDC1 ₃ ) 51.37(d, J=6.8 Hz, 3H), 2.58(s, 3H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.15~7.68(m, 4H)

Example 14: Synthesis of l-(2-fluorophenyl)-(S)-l-methoxymethoxypropyl-(S)-2- propylcarbamate

Ή NMR(400MHz, CDC1 ₃ ) 50.90(t, J=6.8 Hz, 3H), 1.37(d, J=6.8 Hz, 3H), 1.60(m, 2H), 3.18(t, J=7.1Hz, 2H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.15~7.68(m, 4H)

Example 15: Synthesis of l-(2-fluorophenyl)-(S)-l-methoxymethoxypropyl-(S)-2- isopropylcarbamate

1H NMR(400MHz, CDC1 ₃ ) δ, 1.27(d, J=6.8 Hz, 6H), 1.37(d, J=6.8 Hz, 3H), 3.30(s, 3H), 4.17(m, 1H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.15~7.69(m, 4H)

Example 16: Synthesis of l-(2-fluorophenyl)-(S)-l-methoxymethoxypropyl-(S)-2- cyclopropylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 60.57(m, 2H), 0.82(m, 2H), 1.37(d, J=6.8 Hz, 3H), 2.75(m, 1H), 3.30(s, 3H), 4.7 l(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.16~7.70(m, 4H)

Example 17: Synthesis of l-(2-fluorophenyl)-(S)-l-methoxymethoxypropyl-(S)-2- cyclohexylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 51.11-1.21 (m, 4H), 1.37(d, J=6.8 Hz, 3H), 1.47~1.49(m, 4H), 1.74(m, 2H), 3.30(s, 3H), 3.54(m, 1H), 4.71 (d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.15~7.66(m, 4H)

Example 18: Synthesis of l-(2-fluorophenyl)-(S)-l-methoxymethoxypropyl-(S)-2- cyclohexylcarbamate

Ή NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8 Hz, 3H), 3.30(s, 3H), 4.20(m, 2H), 4.71(d, J=6.8, 1 H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.15~7.68(m, 4H), 7.72~7.88(m, 5H)

Example 19 : Synthesis of l-(2fluorophenyl)-(S)-l-methoxymethoxypropyl-(S)-2- bicyclo [2,2, 1 ] heptanescarb amate

1H NMR(400MHz, CDC1 ₃ ) 61.33~1.58(m, 9H), 1.75~1.88(m, 2H), 2.06-2.13(m, 2H), 3.30(s, 3H), 3.53(m, 1H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.15~7.68(m, 4H), 7.37~7.88(m, 5H)

Example 20 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxypropyl-(S)-2- carbamate

Ή N R(400MHz, CDC1 ₃ ) 81.37(d, J=6.8 Hz, 3H), 3.30(s, 3H), 4.7 l(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.13~7.88(m, 4H)

Example 21 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxypropyl-(S)-2- methylcarbamate

Ή NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8 Hz, 3H), 2.58(s, 3H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.13~7.898(m, 4H)

Example 22 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxypropyl-(S)-2- propylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 50.90(t, J=6.8 Hz, 3H), 1.37(d, J=6.8 Hz, 3H), 1.60(m, 2H), 3.18(t, J=7.1Hz, 2H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.14~7.87(m, 4H)

Example 23 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxypropyl-(S)-2- isopropylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 5, 1.27(d, J=6.8 Hz, 6H), 1.37(d, J=6.8 Hz, 3H), 3.30(s, 3H), 4.17(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.15~7.89(m, 4H)

Example 24 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxypropyl-(S)-2 cyclopropylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 60.57(m, 2H), 0.82(m, 2H), 1.37(d, J=6.8 Hz, 3H), 2.750 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.16~7.87(m, 4H)

Example 25 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxypropyl-(S)-2- cyclohexylcarbamate

Ή NMR(400MHz, CDC1 ₃ ) 51.11-1.21 (m, 4H), 1.37(d, J=6.8 Hz, 3H), 1.47~1.49(m, 4H), 1.74(m, 2H), 3.30(s, 3H), 3.54(m, 1H), 4.71(d, J=6.8, IH), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.18-7.9 l(m, 4H)

Example 26 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxypropyl-(S)-2- cyclohexylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8 Hz, 3H), 3.30(s, 3H), 4.20(m, 2H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.15~7.68(m, 4H), 7.72~7.88(m, 5H)

Example 27 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxypropyl-(S)-2- bicyclo[2,2,l]heptanescarbamate

1H NMR(400MHz, CDC1 ₃ ) 51.33~1.58(m, 9H), 1.75~1.88(m, 2H), 2.06-2.13(m, 2H), 3.30(s, 3H), 3.53(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.15~7.68(m, 4H), 7.37~7.88(m, 5H)

Example 28 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxybutyl-(S)-2- carbam

Ή NMR(400MHz, CDC1 ₃ ) 51.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 29: Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxybutyl-(S)-2- methylcarbamate

Ή NMR(400MHz, CDC1 ₃ ) 61.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 2.58(s, 3H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.13~7.88(m, 4H)

Example 30 : Synthesis of l-(2-iodophenyI)-(S)-l-methoxymethoxybutyl-(S)-2- propylcarbamate

Ή NMR(400MHz, CDC1 ₃ ) 60.90(t, J=6.8 Hz, 3H), 1.04(t, J=7.6Hz, 3H), 1.58-1.71 (m, 4H), 3.18(t, J=7.1Hz, 2H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.14~7.89(m, 4H)

Example 31 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxybutyl-(S)-2 isopropylcarbamate Ή NMR(400MHz, CDC1 ₃ ) 51.04(t, J=7.6Hz, 3H), 1.27(d, J=6.8 Hz, 6H), 1.60~1.71(m, 2H), 3.30(s, 3H), 4.17(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.15~7.90(m, 4H)

Example 32 : Synthesis of l-(2-iodophenyI)-(S)-l-methoxymethoxybutyl-(S)-2- cyclopropylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 50.57(m, 2H), 0.82(m, 2H), 1.04(t, J=7.6Hz, 3H), 1.60-1.7 l(m, 2H), 2.75(m, IH), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.16~7.90(m, 4H)

Example 33: Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxybutyl-(S)-2- cyclohexylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 61.04(t, J=7.6Hz, 3H), 1.11-1.21 (m, 4H), 1.47~1.49(m, 4H), 1.60~1.71(m, 2H), 1.74(m, 2H), 3.30(s, 3H), 3.54(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.14~7.87(m, 4H)

Example 34 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxybutyl-(S)-2- cyclohexylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 61.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.30(s, 3H), 4.20(m, 2H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.14-7.19(m, 4H), 7.37~7.88(m, 5H) Example 35 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxybutyl-(S)-2- bicyclo[2,2,l]heptanescarbamate

1H NMR(400MHz, CDC1 ₃ ) 51.04(t, J=7.6Hz, 3H), 1.33~1.58(m, 6H), 1.60-1.71 (m, 2H), 1.75~1.88(m, 2H), 2.06~2.13(m, 2H), 3.30(s, 3H), 3.53(m, 1H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.15~7.19(m, 4H), 7.37~7.88(m, 5H)

Example 36 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxy-3-methyl-butyI- (S)-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.07(d, J=7.6Hz, 3H), 1.83-1.89(m, 1H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 37 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxy-3-methyl-butyl- (S)-2-methylcarbamate

Ή NMR(400MHz, CDC1 ₃ ) 51.04(d, J=7.6Hz, 6H), 1.60~1.71(m, 1H), 2.58(s, 3H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.13~7.88(m, 4H)

Example 38 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxy-3-methyl-butyl- (S)-2-propylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 50.90(t, J=6.8 Hz, 3H), 1.04(d, J=7.6Hz, 6H), 1.58-1.7 l(m, 5H), 3.18(t, J=7.1Hz, 2H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.14~7.89(m, 4H)

Example 39 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxy-3-methyl-butyl- (S)-2-isopropylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 61.04(t, J=7.6Hz, 6H), 1.27(d, J=6.8 Hz, 6H), 1.60~1.71(m, IH), 3.30(s, 3H), 4.17(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.15~7.90(m, 4H)

Example 40 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxy-3-methyl-butyl- (S)-2-cyclopropylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 60.57(m, 2H), 0.82(m, 2H), 1.04(d, J=7.6Hz, 6H), 1.60~1.71(m, IH), 2.75(m, IH), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.16~7.90(m, 4H)

Example 41 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxy-3-methyl-butyl- (S)-2-cyclohexylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 61.04(d, J=7.6Hz, 6H), 1.11-1.21 (m, 4H), 1.47~1.49(m, 4H), 1.74(m, 2H), 1.84~1.90(m, IH), 3.30(s, 3H), 3.54(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.14~7.87(m, 4H)

Example 42 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxy-3-methyI-butyI- (S)-2-cyclohexylcarbamate

Ή NMR(400MHz, CDC1 ₃ ) 61.04(d, J=7.6Hz, 6H), 1.87~1.90(m, IH), 3.30(s, 3H), 4.20(m, 2H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.14~7.19(m, 4H), 7.37~7.88(m, 5H)

Example 43 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxy-3-methyl-butyl- (S)-2-bicyclo[2,2,l]heptanescarbamate

1H NMR(400MHz, CDC1 ₃ ) 61.04(d, J=7.6Hz, 6H), 1.33~1.58(m, 6H), 1.75~1.88(m, 2H), 1.88~1.93(m, IH), 2.06~2.13(m, 2H), 3.30(s, 3H), 3.53(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.15~7.19(m, 4H), 7.37~7.88(m, 5H)

Example 44 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxyhexyl-(S)-2- carbamate

Ή NMR(400MHz, CDC1 ₃ ) 50.84(t, J=7.0Hz, 3H), 1.20~1.35(m, 4H), 1.36~1.41(m, IH), 1.59~1.63(m, IH), 3.30(s, 3H), 4.47(br s, 2H), 4.71 (d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 45: Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxyhexyl-(S)-2- methylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 50.89(t, J=7.2Hz, 3H), 1.20~1.35(m, 4H), 1.36-1.41 (m, IH), 1.59~1.63(m, IH), 2.58(s, 3H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.13~7.88(m, 4H)

Example 46 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxyhexyl-(S)-2- propylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 50.87(t, J=6.8Hz, 3H), 0.90(t, J=6.8Hz, 3H), 1.21~1.35(m, 4H), 1.36~1.40(m, IH), 1.58~1.62(m, IH), 3.18(t, J=7.1Hz, 2H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.14~7.89(m, 4H)

Example 47 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxyhexyl-(S)-2- isopropylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 50.84(t, J=7.6Hz, 3H), 1.22~1.35(m, 4H), 1.27(d, J=6.8 Hz, 6H), 1.36~1.40(m, IH), 1.58~1.62(m, IH), 3.30(s, 3H), 4.17(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.15~7.90(m, 4H)

Example 48 : Synthesis of l-(2-iodophenyI)-(S)-l-methoxymethoxyhexyl-(S)-2- cyclopropylcarbamate

Ή NMR(400MHz, CDC1 ₃ ) 60.57(m, 2H), 0.82(m, 2H), 0.88(t, J=7.6Hz, 3H), 1.22~1.35(m, 4H), 1.36~1.40(m, IH), 1.58~1.62(m, IH), 2.75(m, IH), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.16~7.90(m, 4H)

Example 49 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxyhexyl-(S)-2- cyclohexylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 60.98(t, J=7.6Hz, 3H), 1.11-1.21 (m, 4H), 1.26~1.33(m, 4H), 1.47~1.49(m, 2H), 1.52~1.54(m, 2H), 1.74(m, 2H), 1.84~1.90(m, IH), 3.30(s, 3H), 3.54(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.14~7.87(m, 4H)

Example 50 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxyhexyl-(S)-2- cyclohexylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 50.94(t, J=7.6Hz, 3H), 1.26~1.33(m, 4H), 1.51~1.55(m, 2H), 3.30(s, 3H), 4.20(m, 2H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.14~7.19(m, 4H), 7.37~7.88(m, 5H)

Example 51 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxyhexyl-(S)-2- bicyclo[2,2,l]heptanescarbamate

1H NMR(400MHz, CDC1 ₃ ) 60.97(t, J=7.0Hz, 3H), 1.25~1.32(m, 4H), 1.33~1.58(m, 8H), 1.60~1.71(m, 2H), 1.75~1.88(m, 2H), 2.06~2.13(m, 2H), 3.30(s, 3H), 3.53(m, 1H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.15~7.19(m, 4H), 7.37~7.88(m, 5H)

Example 52: Synthesis of l-(3-iodophenyl)-(S)-l-methoxymethoxypropyl-(S)-2- carb

Ή NMR(400MHz, CDC1 ₃ ) 51.16(d, J=6.4Hz, 3H), 3.39(s, 3H), 4.54~4.63(m, 6H), 5.04~5.10(m, 1H), 7.09~7.73(m, 4H)

Example 53: Synthesis of l-(3-iodophenyl)-(S)-l-methoxymethoxybutyl-(S)-2- carbamate

H NMR(400MHz, CDC1 ₃ ) 51.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 5.45(s, 2H), 6.96~7.57(m, 4H)

Example 54: Synthesis of l-(3-iodophenyl)-(S)-l-methoxymethoxy-3-methyl-butyI- (S)-2-carbamate

H NMR(400MHz, CDC1 ₃ ) 61.07(t, J=7.6Hz, 6H), 1.83~1.89(m, IH), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 5.45(s, 2H), 7.00~7.58(m, 4H)

Example 55: Synthesis of l-(3-iodophenyl)-(S)-l-methoxymethoxyhexyl-(S)-2- carbamate

Ή NMR(400MHz, CDC1 ₃ ) 50.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 3.30(s, 3H), 4.71 (d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 5.45(s, 2H), 7.01~7.59(m, 4H)

Example 56: Synthesis of l-(4-fluorophenyl)-(S)-l-methoxymethoxypropyl-(S)-2- carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.37(d, J=6.8 Hz, 3H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 6.96~7.17(m, 4H) Example 57 : Synthesis of l-(4-fluorophenyl)-(S)-l-methoxymethoxybutyl-(S)-2- carba

Ή NMR(400MHz, CDC1 ₃ ) 51.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 5.45(s, 2H), 6.90~7.20(m, 4H)

Example 58 : Synthesis of l-(4-fluorophenyl)-(S)-l-methoxymethoxy-3-methyl- butyl-(S -2-carbamate

Ή NMR(400MHz, CDC1 ₃ ) 61.07(t, J=7.6Hz, 6H), 1.83~1.89(m, IH), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 5.45(s, 2H), 6.92~7.17(m, 4H)

Example 59 : Synthesis of l-(4-fluorophenyl)-(S)-l-methoxymethoxyhexyl-(S)-2- carba

^] H NMR(400MHz, CDC1 ₃ ) 80.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 5.45(s, 2H), 6.96~7.19(m, 4H)

Example 60 : Synthesis of l-(2,4-dichlorophenyl)-(S)-l-methoxymethoxypropyl-(S)- 2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.37(d, J=6.8Hz, 3H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.24~7.30(m, 2H), 7.73(d, J=1.5Hz, IH)

Example 61 : Synthesis of l-(2,4-dichlorophenyl)-(S)-l-methoxymethoxybutyl-(S)- 2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 5.45(s, 2H), 7.24~7.30(m, 2H), 7.73(d, J=1.5Hz, IH)

Example 62 : Synthesis of l-(2,4-dichlorophenyl)-(S)-l-methoxymethoxy-3-methyl- butyl-(S -2-carbamate

Ή NMR(400MHz, CDC1 ₃ ) 61.07(t, J=7.6Hz, 6H), 1.83~1.89(m, IH), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 5.45(s, 2H), 7.24~7.30(m, 2H), 7.73(d, J=1.5Hz, IH)

Example 63 : Synthesis of l-(2,4-dichlorophenyl)-(S)-l-methoxymethoxyhexyl-(S)- 2-carba

1H NMR(400MHz, CDC1 ₃ ) 50.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.24~7.30(m, 2H), 7.73(d, J=1.5Hz, 1H)

Example 64: Synthesis of l-(2,6-dichlorophenyl)-(S)-l-methoxymethoxypropyl-(S)- 2-carba

Ή NMR(400MHz, CDC1 ₃ ) 51.37(d, J=6.8Hz, 3H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.57~7.58(m, 3H)

Example 65 : Synthesis of l-(2,6-dichlorophenyl)-(S)-l-methoxymethoxybutyl-(S)- 2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 61.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.54~7.57(m, 3H)

Example 66 : Synthesis of l-(2,6-dichlorophenyI)-(S)-l-methoxymethoxy-3-methyl- butyl-(S)-2-carbamate

Ή NMR(400MHz, CDC1 ₃ ) 61.07(t, J=7.6Hz, 6H), 1.83~1.89(m, 1H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.55~7.57(m, 3H)

Example 67 : Synthesis of l-(2,4-dichlorophenyl)-(S)-l-methoxymethoxyhexyl-(S)- 2-carbamate

Ή NMR(400MHz, CDC1 ₃ ) 60.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 3.30(s, 3H), 4.71 (d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 5.45(s, 2H), 7.54~7.59(m, 3H)

Example 68 : Synthesis of l-(2,3-dichlorophenyl)-(S)-l-methoxymethoxypropyl-(S)- 2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.37(d, J=6.8Hz, 3H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H),7.01~7.14(m, 3H)

Example 69: Synthesis of l-(2-chlorophenyl)-(R)-l-methoxymethoxypropyl-(R)-2- carb

l NMR(400MHz, CDC1 ₃ ) 81.37(d, J=6.8 Hz, 3H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 70: Synthesis of l-(2-chlorophenyl)-l-methoxymethoxypropyl-2- carbama

Ή NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8 Hz, 3H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.26~7.70(m, 4H) Example 71: Synthesis of l-(2-chlorophenyl)-(R)-l-methoxymethoxypropyl-(S)-2- carbamate

lH NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8 Hz, 3H), 3.30(s, 3H), 4.71 (d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 72 : Synthesis of l-(2-chlorophenyl)-(S)-l-methoxymethoxypropyl-(R)-2- carba

1H NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8 Hz, 3H), 3.30(s, 3H), 4.71 (d, 7=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 73 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxymethoxybutyl-(R)-2- carbam

1H NMR(400MHz, CDC1 ₃ ) 51.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 74 : Synthesis of l-(2-chlorophenyl)-l-methoxymethoxybutyl-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 61.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 75 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxymethoxy-3-methyl- butyl-( -2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 61.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 76 : Synthesis of l-(2-chlorophenyl)-l-methoxymethoxy-3-methyl-butyl-2- carba

Ή NMR(400MHz, CDC1 ₃ ) 51.07(t, J=7.6Hz, 6H), 1.83~1.89(m, 1H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 77 : Synthesis of lr(2-chlorophenyl)-(R)-l-methoxymethoxyhexyl-(R)-2- carbamate

1H NMR(400MHz, CDC1 ₃ ) 50.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 78 : Synthesis of l-(2-chlorophenyl)-l-methoxymethoxyhexyl-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 50.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 79 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxymethoxypropyl-(R)-2- methylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 51.37(d, J=6.8 Hz, 3H), 2.58(s, 3H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 80 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxymethoxypropyl-(R)-2- propylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 60.90(t, J=6.8 Hz, 3H), 1.37(d, J=6.8 Hz, 3H), 1.60(m, 2H), 3.18(t, J=7.1Hz, 2H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 81 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxymethoxypropyl-(R)-2- isopropylcarbamate

1H NMR(400MHz, CDC1 ₃ ) δ, 1.27(d, J=6.8 Hz, 6H), 1.37(d, J=6.8 Hz, 3H), 3.30(s, 3H), 4.17(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 82 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxymethoxypropyl-(R)-2- cyclopropylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 50.57(m, 2H), 0.82(m, 2H), 1.37(d, J=6.8 Hz, 3H), 2.75(m, IH), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 83 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxymethoxypropyl-(R)-2- cyclohexylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 61.11-1.21 (m, 4H), 1.37(d, J=6.8 Hz, 3H), 1.47~1.49(m, 4H), 1.74(m, 2H), 3.30(s, 3H), 3.54(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 84 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxymethoxypropyl-(R)-2- cyclohexylcarb amate

1H NMR(400MHz, CDC1 ₃ ) 51.37(d, J=6.8 Hz, 3H), 3.30(s, 3H), 4.20(m, 2H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.13~7.19(m, 4H), 7.37~7.88(m, 5H)

Example 85 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxymethoxypropyl-(R)-2- bicyclo [2,2,1] hep tanescarbamate

1H NMR(400MHz, CDC1 ₃ ) 51.33~1.58(m, 9H), 1.75~1.88(m, 2H), 2.06-2.13(m, 2H), 3.30(s, 3H), 3.53(m, 1H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.13~7.19(m, 4H), 7.37~7.88(m, 5H)

Example 86 : Synthesis of l-(2-fluorophenyI)-(R)-l-methoxymethoxypropyl-(R)-2- carbam

1H NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8 Hz, 3H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.15~7.68(m, 4H)

Example 87 : Synthesis of l-(4-fluorophenyl)-(R)-l-methoxymethoxypropyl-(R)-2- carbam

1H NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8 Hz, 3H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 6.96~7.17(m, 4H)

Example 88 : Synthesis of l-(4-fluorophenyl)-(R)-l-methoxymethoxybutyl-(R)-2- carbam

1H NMR(400MHz, CDC1 ₃ ) 51.04(t, J=7.6Hz, 3H), 1.60-1.7 l(m, 2H), 3.30(s, 3H), 4.7 l(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 5.45(s, 2H), 6.90~7.20(m, 4H)

Example 89 : Synthesis of l-(4-fluorophenyl)-(R)-l-methoxymethoxy-3-methyl- butyl-(R -2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.07(t, J=7.6Hz, 6H), 1.83~1.89(m, 1H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 5.45(s, 2H), 6.92~7.17(m, 4H)

Example 90 : Synthesis of l-(4-fluorophenyl)-(R)-l-methoxymethoxyhexyl-(R)-2- carb

1H NMR(400MHz, CDC1 ₃ ) 50.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 3.30(s, 3H), 4.71 (d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 5.45(s, 2H), 6.96~7.19(m, 4H)

Example 91 : Synthesis of l-(2-iodophenyl)-(R)-l-methoxymethoxypropyl-(R)-2- carb

1H NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8 Hz, 3H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.13~7.88(m, 4H)

Example 92 : Synthesis of l-(2-iodophenyl)-(R)-l-methoxymethoxybutyl-(R)-2- carbamate O^ H ₂

1H NMR(400MHz, CDC1 ₃ ) 51.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 93 : Synthesis of l-(2-iodophenyl)-(R)-l-methoxymethoxy-3-methyl-butyl- (R)-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.07(d, J=7.6Hz, 3H), 1.83~1.89(m, IH), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 94 : Synthesis of l-(2-iodophenyl)-(R)-l-methoxymethoxyhexyl-(R)-2- carb

1H NMR(400MHz, CDC1 ₃ ) 60.84(t, J=7.0Hz, 3H), 1.20~1.35(m, 4H), 1.36~1.41(m, IH), 1.59~1.63(m, IH), 3.30(s, 3H), 4.47(br s, 2H), 4.7 l(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 95 : Synthesis of l-(3-iodophenyl)-(R)-l-methoxymethoxypropyl-(R)-2- carbam

1H NMR(400MHz, CDC1 ₃ ) 61.16(d, J=6.4Hz, 3H), 3.39(s, 3H), 4.54~4.63(m, 6H), 5.04~5.10(m, IH), 7.09~7.73(m, 4H)

Example 96 : Synthesis of l-(3-iodophenyl)-(R)-l-methoxymethoxybutyl-(R)-2- carbam

Ή NMR(400MHz, CDC1 ₃ ) 51.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 97 : Synthesis of l-(3-iodophenyl)-(R)-l-methoxymethoxy-3-methyl-butyl- (R)-2-carbamate

Ή NMR(400MHz, CDC1 ₃ ) 51.07(d, J=7.6Hz, 3H), 1.83-1.89(m, IH), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 98 : Synthesis of l-(3-iodophenyl)-(R)-l-methoxymethoxyhexyl-(R)-2- carba

1H NMR(400MHz, CDC1 ₃ ) 80.84(t, J=7.0Hz, 3H), 1.20~1.35(m, 4H), 1.36~1.41(m, IH), 1.59~1.63(m, IH), 3.30(s, 3H), 4.47(br s, 2H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 99 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxymethoxypropyl-(R)-2- methylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8 Hz, 3H), 2.58(s, 3H), 3.30(s, 3H), 4.71 (d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 100 : Synthesis of l-(2-chIorophenyl)-(R)-l-methoxymethoxypropyl-(R)-2- propylcarbamate

Ή NMR(400MHz, CDC1 ₃ ) 50.90(t, J=6.8 Hz, 3H), 1.37(d, J=6.8 Hz, 3H), 1.60(m, 2H), 3.18(t, J=7.1Hz, 2H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 101 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxymethoxypropyl-(R)-2- isopropylcarbamate

Ή NMR(400MHz, CDC1 ₃ ) 5, 1.27(d, J=6.8 Hz, 6H), 1.37(d, J=6.8 Hz, 3H), 3.30(s, 3H), 4.17(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 102 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxymethoxypropyl-(R)-2- cyclopropylcarbamate

Ή NMR(400MHz, CDC1 ₃ ) 60.57(m, 2H), 0.82(m, 2H), 1.37(d, J=6.8 Hz, 3H), 2.75(i 3.30(s, 3H), 4.71 (d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 103 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxymethoxypropyl-(R)-2- cyclohexylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 61.11-1.21 (m, 4H), 1.37(d, J=6.8 Hz, 3H), 1.47~1.49(m, 4H), 1.74(m, 2H), 3.30(s, 3H), 3.54(m, 1H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 104 : Synthesis of l-(2-chlorophenyI)-(R)-l-methoxymethoxypropyl-(R)-2- cyclohexylcarbamate

Ή NMR(400MHz, CDC1 ₃ ) 51.37(d, J=6.8 Hz, 3H), 3.30(s, 3H), 4.20(m, 2H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.13~7.19(m, 4H), 7.37~7.88(m, 5H)

Example 105 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxymethoxypropyl-(R)-2- bicyclo[2,2,l]heptanescarbamate

1H NMR(400MHz, CDC1 ₃ ) 61.33~1.58(m, 9H), 1.75~1.88(m, 2H), 2.06~2.13(m, 2H), 3.30(s, 3H), 3.53(m, 1H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.13~7.19(m, 4H), 7.37~7.88(m, 5H)

Example 106 : Synthesis of l-(2,4-dichlorophenyl)-(R)-l-methoxymethoxypropyl- (R)-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8Hz, 3H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.24~7.30(m, 2H), 7.73(d, J=1.5Hz, IH)

Example 107 : Synthesis of l-(2,6-dichlorophenyl)-(R)-l-methoxymethoxypropyl- (R)-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.37(d, J=6.8Hz, 3H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.57~7.58(m, 3H)

Example 108 : Synthesis of l-(2,3-dichlorophenyl)-(R)-l-methoxymethoxypropyl- (R)-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.37(d, J=6.8Hz, 3H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H),7.01~7.14(m, 3H)

Example 109 : Synthesis of l-(2,4-dichlorophenyl)-(R)-l-methoxymethoxybutyl- (R)-2-carbamate

Ή NMR(400MHz, CDC1 ₃ ) 61.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 5.45(s, 2H), 7.24~7.30(m, 2H), 7.73(d, J=1.5Hz, IH)

Example 110 : Synthesis of l-(2,6-dichlorophenyl)-(R)-l-methoxymethoxybutyl-(R)- 2-carba

1H NMR(400MHz, CDC1 ₃ ) 81.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 5.45(s, 2H), 7.54~7.57(m, 3H)

Example 111 : Synthesis of l-(2,4-dichlorophenyl)-(R)-l-methoxymethoxy-3- methyl-butyl-(R)-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 61.07(t, J=7.6Hz, 6H), 1.83~1.89(m, IH), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 5.45(s, 2H), 7.24~7.30(m, 2H), 7.73(d, J=1.5Hz, IH)

Example 112 : Synthesis of l-(2,6-dichlorophenyl)-(R)-l-methoxymethoxy-3- methyl-butyl-(R)-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.07(t, J=7.6Hz, 6H), 1.83~1.89(m, IH), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 5.45(s, 2H), 7.55~7.57(m, 3H)

Example 113 : Synthesis of l-(2,4-dichlorophenyl)-(R)-l-methoxymethoxyhexyl- (R)-2-carbamate

Ή NMR(400MHz, CDC1 ₃ ) 50.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 5.45(s, 2H), 7.24~7.30(m, 2H), 7.73(d, J=1.5Hz, IH)

Example 114 : Synthesis of l-(2,4-dichlorophenyl)-(R)-l-methoxymethoxyhexyl- (R)-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 60.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 5.45(s, 2H), 7.54~7.59(m, 3H)

Example 115 : Synthesis of l-(2,4-dichlorophenyl)-l-methoxymethoxypropyl-2- carbamate

Ή NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8Hz, 3H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.24~7.30(m, 2H), 7.73(d, J=1.5Hz, IH)

Example 116 : Synthesis of l-(2,6-dichlorophenyl)-l-methoxymethoxypropyl-2- carbam

Ή NMR(400MHz, CDC1 ₃ ) 51.37(d, J=6.8Hz, 3H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.57~7.58(m, 3H)

Example 117 : Synthesis of l-(2,3-dichlorophenyl)-l-methoxymethoxypropyl-2-

1H NMR(400MHz, CDC1 ₃ ) 51.37(d, J=6.8Hz, 3H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H),7.01~7.14(m, 3H)

Example 118 : Synthesis of l-(2,4-dichlorophenyl)-l-methoxymethoxybutyl-2- carbam

Ή NMR(400MHz, CDC1 ₃ ) 51.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 5.45(s, 2H), 7.24~7.30(m, 2H), 7.73(d, J=1.5Hz, IH)

Example 119 : Synthesis of l-(2,6-dichlorophenyl)-l-methoxymethoxybutyl-2- carbamat

1H NMR(400MHz, CDC1 ₃ ) 61.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 5.45(s, 2H), 7.54~7.57(m, 3H)

Example 120 : Synthesis of l-(2,4-dichlorophenyl)-l-methoxymethoxy-3-methyl- butyl-2-carbamate O^ .NH ₂

CI l NMR(400MHz, CDC1 ₃ ) 61.07(t, J=7.6Hz, 6H), 1.83~1.89(m, IH), 3.30(s, 3H), 4.7 l(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 5.45(s, 2H), 7.24~7.30(m, 2H), 7.73(d, J=1.5Hz, IH)

Example 121 : Synthesis of l-(2,6-dichlorophenyI)-l-methoxymethoxy-3-methyl- butyl-2-carbamate

Ή NMR(400MHz, CDC1 ₃ ) 51.07(t, J=7.6Hz, 6H), 1.83~1.89(m, IH), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 5.45(s, 2H), 7.55~7.57(m, 3H)

Example 122 : Synthesis of l-(2,4-dichlorophenyl)-l-methoxymethoxyhexyl-2- carbamate

1H NMR(400MHz, CDC1 ₃ ) 60.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 3.30(s, 3H), 4.71 (d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 5.45(s, 2H), 7.24~7.30(m, 2H), 7.73(d, J=1.5Hz, IH)

Example 123 : Synthesis of l-(2,4-dichlorophenyl)-l-methoxymethoxyhexyl-2- carbam

1H NMR(400MHz, CDC1 ₃ ) 60.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.54~7.59(m, 3H)

Example 124 : Synthesis of l-(2-chlorophenyl)-(S)-l-methoxypropyl-(S)-2- carbamate

l-(2-chlorophenyl)-l-hydorxyalkyl-2-alkylcarbamate(Preparati on Example 103, 0.5g), THF(Tetrahydrofuran), MeI(Methyliodide, 5eq, 0.5ml) and t-BuOH(Potassium tert-butoxide, 1.5eq, 0.26g) were put into a flask and stirred at the 0 ^° C . When the reaction was completed, the obtained product was washed with 1M HCl solution and EA(Ethylacetate). The separated organic layer was dehydrated with anhydrous MgS0 ₄ (Magnesium sulfate), filtrated, and concented under reduced pressure. The concentrated residue was purified by a silicagel aolumn chromatography, to obtain title compound.

1H NMR(400MHz, CDC1 ₃ ) 61.40(d, J=6.0Hz, 3H), 3.24(s, 3H), 4.71(d, J=6.4Hz, 1H), 4.80~4.85(m, 1H), 7.01(br s, 1H), 7.07~7.20(m, 4H)

According to the method described in Example 124, the following compounds of Examples 124 to 123246 were prepared:

Example 125 : Synthesis of l-(2-chlorophenyl)-(S)-l-methoxypropyl-(S)-2- methylcarbamate

Ή NMR(400MHz, CDC1 ₃ ) 51.40(d, J=6.0Hz, 3H), 2.74(s, 3H), 3.24(s, 3H), 4.7 l(d, J=6.4Hz, 1H), 4.80~4.85(m, 1H), 7.01(br s, 1H), 7.07~7.20(m, 4H) Example 126 : Synthesis of l-(2-chlorophenyl)-(S)-l-methoxypropyl-(S)-2- propylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 50.96(t, J=6.4Hz, 3H), 1.40(d, J=6.0Hz, 3H), 1.55~1.60(m, 2H), 2.96(t, J=6.0Hz, 2H), 3.24(s, 3H), 4.71(d, J=6.0Hz, 1H), 4.82~4.88(m, 1H), 6.76(br s, 2H), 7.07-7.2 l(m, 4H)

Example 127 : Synthesis of l-(2-chlorophenyl)-(S)-l-methoxypropyl-(S)-2- isopropylcarbamate

1H NMR(400MHz, CDC1 ₃ ) δ, 1.15(d, J=6.0Hz, 3H), 1.35(d, J=6.4Hz, 3H), 1.50(d, J=6.8Hz, 3H), 3.24(s, 3H), 3.75(br s, 1H), 4.48(br s, 1H), 4.50(d, J=4.8Hz, 1H), 5.09~5.20(m, 1H), 7.07~7.20(m, 4H)

Example 128 : Synthesis of l-(2-chlorophenyl)-(S)-l-methoxypropyl-(S)-2- cyclopropylcarbamate

Ή NMR(400MHz, CDC1 ₃ ) 60.30~0.34(m, 2H), 0.54~0.58(m, 2H), 1.30(d, J=6.8Hz, 3H), 2.55(m, 1H), 3.24(s, 3H), 4.55(d, J=4.8Hz, 1H), 4.90(br m, 1H), 5.09~5.15(br s, 1H), 7.06-7.2 l(m, 4H)

Example 129 : Synthesis of l-(2-chlorophenyl)-(S)-l-methoxypropyl-(S)-2- cyclohexylcarb amate

Ή NMR(400MHz, CDC1 ₃ ) 51.11-1.21 (m, 4H), 1.37(d, J=6.8 Hz, 3H), 1.47~1.49(m, 4H), 1.74(m, 2H), 3.30(s, 3H), 3.54(m, 1H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 130 : Synthesis of l-(2-chlorophenyl)-(S)-l-methoxypropyl-(S)-2- cyclohexylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 51.40(d, J=6.8 Hz, 3H), 3.24(s, 3H), 4.20(m, 2H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 7.13~7.19(m, 4H), 7.32~7.46(m, 5H)

Example 131 : Synthesis of l-(2-chlorophenyl)-(S)-l-methoxypropyl-(S)-2- bic clo[2,2,l]heptanescarbamate

Ή NMR(400MHz, CDC1 ₃ ) 51.40(d, J=6.4Hz, 3H), 1.44~1.50(m, 7H), 1.70~1.73(m, 1H), 2.03~2.07(m, 1H), 3.24(s, 3H), 3.50~3.55(m, 2H), 4.71(d, J=6.4Hz, 1H), 4.80~4.87(m, 1H), 7.07-7.19(m, 4H)

Exa nthesis of l-(2-chlorophenyI)-(S)-l-methoxybutyl-(S)-2-carbamate

Ή NMR(400MHz, CDC1 ₃ ) 51.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.22(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 7.26~7.70(m, 4H)

Example 133 : Synthesis of l-(2-chlorophenyl)-(S)-l-methoxy-3-methyl-butyl-(S)-2- carbam

lH NMR(400MHz, CDC1 ₃ ) 61.07(t, J=7.6Hz, 6H), 1.83~1.89(m, IH), 3.26(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 7.26~7.70(m, 4H)

Example 134 : Synthesis of l-(2-chlorophenyl)-(S)-l-methoxyhexyl-(S)-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 60.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 3.23(s, 3H), 4.7 l(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 7.26~7.70(m, 4H)

Example 135 : Synthesis of l-(2-fluorophenyl)-(S)-l-methoxypropyl-(S)-2- carba

Ή NMR(400MHz, CDC1 ₃ ) 51.37(d, J=6.8 Hz, 3H), 3.23(s, 3H), 4.7 l(d, J=6.8, IH), 4.82~4.88(m, IH), 7.15~7.68(m, 4H)

Example 136 : Synthesis of l-(2-fluorophenyl)-(S)-l-methoxypropyl-(S)-2- methylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8 Hz, 3H), 2.58(s, 3H), 3.24(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.15~7.68(m, 4H)

Example 137 : Synthesis of l-(2-fluorophenyI)-(S)-l-methoxypropyl-(S)-2- propylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 60.90(t, J=6.8 Hz, 3H), 1.37(d, J=6.8 Hz, 3H), 1.60(m, 2H), 3.18(t, J=7.1Hz, 2H), 3.22(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.15~7.68(m, 4H)

Example 138 : Synthesis of l-(2-fluorophenyl)-(S)-l-methoxypropyl-(S)-2- isopropylcarbamate

1H NMR(400MHz, CDC1 ₃ ) δ, 1.27(d, J=6.8 Hz, 6H), 1.37(d, J=6.8 Hz, 3H), 3.25(s, 3H), 4.17(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.15~7.69(m, 4H)

Example 139 : Synthesis of l-(2-fluorophenyl)-(S)-l-methoxypropyl-(S)-2- cyclopropylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 60.57(m, 2H), 0.82(m, 2H), 1.37(d, J=6.8 Hz, 3H), 2.75(m, IH), 3.24(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.16~7.70(m, 4H) Example 140 : Synthesis of l-(2-fluorophenyl)-(S)-l-methoxypropyl-(S)-2- cyclohexylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 51.11-1.21 (m, 4H), 1.37(d, J=6.8 Hz, 3Η), 1.47~1.49(m, 4H), 1.74(m, 2H),.3.26(s, 3H), 3.54(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.15~7.66(m, 4H)

Example 141 : Synthesis of l-(2-fluorophenyl)-(S)-l-methoxymethoxypropyl-(S)-2- cyclohexylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8 Hz, 3H), 3.24(s, 3H), 4.20(m, 2H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.15~7.68(m, 4H), 7.72~7.88(m, 5H)

Example 142 : Synthesis of l-(2fluorophenyl)-(S)-l-methoxypropyl-(S)-2- bicyclo[2,2,l]heptanescarbamate

1H NMR(400MHz, CDC1 ₃ ) 61.33~1.58(m, 9H), 1.75~1.88(m, 2H), 2.06~2.13(m, 2H), 3.23(s, 3H), 3.53(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.15~7.68(m, 4H), 7.37~7.88(m, 5H)

Example 143 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxypropyl-(S)-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8 Hz, 3Η), 3.21(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.13~7.88(m, 4H)

Example 144 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxypropyl-(S)-2- methylcarbamate

Ή NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8 Hz, 3H), 2.58(s, 3H), 3.24(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.13~7.898(m, 4H)

Example 145 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxypropyl-(S)-2- propylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 60.90(t, J=6.8 Hz, 3H), 1.37(d, J=6.8 Hz, 3H), 1.60(m, 2H), 3.18(t, J=7.1Hz, 2H), 3.24(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.14~7.87(m, 4H)

Example 146 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxypropyl-(S)-2- isopropylcarbamate

1H NMR(400MHz, CDC1 ₃ ) δ, 1.27(d, J=6.8 Hz, 6H), 1.37(d, J=6.8 Hz, 3H), 3.30(s, 3H), 4.17(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.15~7.89(m, 4H) Example 147 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxypropyl-(S)-2- cyclopro lcarbamate

1H NMR(400MHz, CDC1 ₃ ) 60.57(m, 2H), 0.82(m, 2H), 1.37(d, J=6.8 Hz, 3Η), 2.75(m, IH), 3.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.16~7.87(m, 4H)

Example 148 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxypropyl-(S)-2- cyclohexylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 51.11-1.21 (m, 4H), 1.37(d, J=6.8 Hz, 3H), 1.47~1.49(m, 4H), 1.74(m, 2H), 3.30(s, 3H), 3.54(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.18-7.9 l(m, 4H)

Example 149 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxypropyl-(S)-2- cyclohexylcarbamate

Ή NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8 Hz, 3H), 3.24(s, 3H), 4.20(m, 2H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.15~7.68(m, 4H), 7.72~7.88(m, 5H)

Example 150 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxypropyl-(S)-2- bicyclo[2,2,l]heptanescarbamate

l NMR(400MHz, CDC1 ₃ ) 51.33~1.58(m, 9H), 1.75~1.88(m, 2H), 2.06-2.13(m, 2H), 3.22(s, 3H), 3.53(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.15~7.68(m, 4H), 7.37~7.88(m, 5H)

Example 151 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxybutyl-(S)-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.24(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.26~7.70(m, 4H)

Example Synthesis of l-(2-iodophenyl)-(S)-l-methoxybutyl-(S)-2- lethylcarbamate

Ή NMR(400MHz, CDC1 ₃ ) 61.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 2.58(s, 3H), 3.23(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.13~7.88(m, 4H)

Example Synthesis of l-(2-iodophenyl)-(S)-l-methoxybutyl-(S)-2- propylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 60.90(t, J=6.8 Hz, 3H), 1.04(t, J=7.6Hz, 3H), 1.58-1.7 l(m, 3.18(t, J=7.1Hz, 2H), 3.22(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.14~7.89(m, 4H) Example 154 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxybutyl-(S)-2- isopropylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 61.04(t, J=7.6Hz, 3H), 1.27(d, J=6.8 Hz, 6H), 1.60-1.7 l(i

3.23(s, 3H), 4.17(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.15~7.90(m, 4H)

Example 155 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxybutyl-(S)-2- cyclopropylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 60.57(m, 2H), 0.82(m, 2H), 1.04(t, J=7.6Hz, 3H), 1.60-1.71 (m, 2H), 2.75(m, IH), 3.24(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.16~7.90(m, 4H)

Example 156 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxybutyl-(S)-2- cyclohexylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 51.04(t, J=7.6Hz, 3H), 1.11-1.21 (m, 4H), 1.47~1.49(m, 4H), 1.60~1.71(m, 2H), 1.74(m, 2H), 3.23(s, 3H), 3.54(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.14~7.87(m, 4H)

Example 157 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxybutyl-(S)-2- cyclohexylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 51.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.23(s, 3H), 4.20(m, 2H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.14~7.19(m, 4H), 7.37~7.88(m, 5H)

Example 158 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxybutyl-(S)-2- bicyclo[2,2,l]heptanescarbamate

Ή NMR(400MHz, CDC1 ₃ ) 61.04(t, J=7.6Hz, 3H), 1.33~1.58(m, 6H), 1.60~1.71(m, 2H), 1.75~1.88(m, 2H), 2.06~2.13(m, 2H), 3.24(s, 3H), 3.53(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.15~7.19(m, 4H), 7.37~7.88(m, 5H)

Example 159 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxy-3-methyl-butyl-(S)-2- carbam

1H NMR(400MHz, CDC1 ₃ ) 51.07(d, J=7.6Hz, 3H), 1.83~1.89(m, IH), 3.23(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.26~7.70(m, 4H)

Example 160 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxy-3-methyl-butyl-(S)-2- methylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 61.04(d, J=7.6Hz, 6H), 1.60~1.71(m, IH), 2.58(s, 3H), 3.24(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.13~7.88(m, 4H)

Example 161 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxy-3-methyl-butyl-(S)-2- propylc rbamate

Ή NMR(400MHz, CDC1 ₃ ) 60.90(t, J=6.8 Hz, 3H), 1.04(d, J=7.6Hz, 6Η), 1.58~1.71(m, 5H), 3.18(t, J=7.1Hz, 2H), 3.23(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.14~7.89(m, 4H)

Example 162 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxy-3-methyI-butyI-(S)-2- isopropylcarbamate

Ή NMR(400MHz, CDCI3) 61.04(t, J=7.6Hz, 6H), 1.27(d, J=6.8 Hz, 6H), 1.60~1.71(i

3.24(s, 3H), 4.17(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.15~7.90(m, 4H)

Example 163 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxy-3-methyl-butyl-(S)-2- cyclopropylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 50.57(m, 2H), 0.82(m, 2H), 1.04(d, J=7.6Hz, 6H), 1.60~1.71(m, IH), 2.75(m, IH), 3.24(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.16~7.90(m, 4H)

Example 164 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxy-3-methyl-butyl-(S)-2- cyclohexylcarbamate

Ή NMR(400MHz, CDC1 ₃ ) 61.04(d, J=7.6Hz, 6H), 1.11-1.21 (m, 4H), 1.47~1.49(m, 4H), 1.74(m, 2H), 1.84~1.90(m, 1H), 3.23(s, 3H), 3.54(m, 1H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 7.14~7.87(m, 4H)

Example 165 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxy-3-methyl-butyl-(S)-2- cyclohexylcarbamate

l NMR(400MHz, CDC1 ₃ ) 51.04(d, J=7.6Hz, 6H), 1.87~1.90(m, 1H), 3.24(s, 3H), 4.20(m, 2H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 7.14~7.19(m, 4H), 7.37~7.88(m, 5H)

Example 166 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxy-3-methyl-butyl-(S)-2- bicyclo[ 2,l]heptanescarbamate

1H NMR(400MHz, CDC1 ₃ ) 51.04(d, J=7.6Hz, 6H), 1.33~1.58(m, 6H), 1.75~1.88(m, 2H), 1.88~1.93(m, 1H), 2.06~2.13(m, 2H), 3.22(s, 3H), 3.53(m, 1H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 7.15~7.19(m, 4H), 7.37~7.88(m, 5H)

Exam le 167 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxyhexyl-(S)-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 50.84(t, J=7.0Hz, 3H), 1.20~1.35(m, 4H), 1.36~1.41(m, IH), 1.59~1.63(m, IH), 3.23(s, 3H), 4.47(br s, 2H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.26~7.70(m, 4H)

Example 168 : Synthesis of l-(2-iodophenyI)-(S)-l-methoxyhexyI-(S)-2- methylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 60.89(t, J=7.2Hz, 3H), 1.20~1.35(m, 4H), 1.36~1.41(m, IH), 1.59~1.63(m, IH), 2.58(s, 3H), 3.23(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.13~7.88(m, 4H)

Example 169 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxyhexyl-(S)-2- propylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 50.87(t, J=6.8Hz, 3H), 0.90(t, J=6.8Hz, 3H), 1.21~1.35(m, 4H), 1.36~1.40(m, IH), 1.58~1.62(m, IH), 3.18(t, J=7.1Hz, 2H), 3.24(s, 3H), 4.71 (d, J=6.8, IH), 4.82~4.88(m, IH), 7.14~7.89(m, 4H)

Example 170 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxyhexyl-(S)-2- isopropylcarbamate

Ή NMR(400MHz, CDC1 ₃ ) 50.84(t, J=7.6Hz, 3H), 1.22~1.35(m, 4H), 1.27(d, J=6.8 Hz, 6H), 1.36~1.40(m, IH), 1.58~1.62(m, IH), 3.23(s, 3H), 4.17(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, 1H), 7.15~7.90(m, 4H)

Example 171 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxyhexyl-(S)-2- cyclopropylcarbamate

Ή NMR(400MHz, CDC1 ₃ ) 60.57(m, 2H), 0.82(m, 2H), 0.88(t, J=7.6Hz, 3H), 1.22~1.35(m, 4H), 1.36~1.40(m, 1H), 1.58~1.62(m, 1H), 2.75(m, 1H), 3.23(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 7.16~7.90(m, 4H)

Example 172 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxyhexyl-(S)-2- cyclohexylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 60.98(t, J=7.6Hz, 3H), 1.11-1.21 (m, 4H), 1.26~1.33(m, 4H), 1.47~1.49(m, 2H), 1.52~1.54(m, 2H), 1.74(m, 2H), 1.84~1.90(m, 1H), 3.23(s, 3H), 3.54(m, 1H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 7.14~7.87(m, 4H)

Example 173 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxyhexyl-(S)-2- cyclohexylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 50.94(t, J=7.6Hz, 3H), 1.26~1.33(m, 4H), 1.51~1.55(m, 2H), 3.23(s, 3H), 4.20(m, 2H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 7.14~7.19(m, 4H), 7.37~7.88(m, 5H)

Example 174 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxyhexyl-(S)-2- bicyclo[2,2,l]heptanescarbamate

Ή NMR(400MHz, CDC1 ₃ ) 50.97(t, J=7.0Hz, 3H), 1.25~1.32(m, 4H), 1.33~1.58(m, 8H), 1.60~1.71(m, 2H), 1.75~1.88(m, 2H), 2.06~2.13(m, 2H), 3.24(s, 3H), 3.53(m, 1H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 7.15~7.19(m, 4H), 7.37~7.88(m, 5H)

Example 175 : Synthesis of l-(3-iodophenyl)-(S)-l-methoxypropyl-(S)-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 61.16(d, J=6.4Hz, 3H), 3.24(s, 3H), 4.54~4.63(m, 4H), 5.04~5.10(m, 1H), 7.09~7.73(m, 4H)

Example 176 : Synthesis of l-(3-iodophenyl)-(S)-l-methoxybutyl-(S)-2-carbamate

H NMR(400MHz, CDC1 ₃ ) 51.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.24(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 6.96~7.57(m, 4H)

Example 177 : Synthesis of l-(3-iodophenyl)-(S)-l-methoxy-3-methyl-butyl-(S)-2- carbam

1H NMR(400MHz, CDC1 ₃ ) 51.07(t, J=7.6Hz, 6H), 1.83~1.89(m, 1H), 3.24(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 7.00~7.58(m, 4H)

Example 178 : Synthesis of l-(3-iodophenyl)-(S)-l-methoxyhexyl-(S)-2-carbamate

Ή NMR(400MHz, CDC1 ₃ ) 60.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 3.23(s, 3H), 4.7 l(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 7.01~7.59(m, 4H)

Example 179 : Synthesis of l-(4-fluorophenyI)-(S)-l-methoxypropyl-(S)-2- carbamate

Ή NMR(400MHz, CDC1 ₃ ) 51.37(d, J=6.8 Hz, 3H), 3.23(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 6.96~7.17(m, 4H)

Example 180 : Synthesis of l-(4-fluorophenyI)-(S)-l-methoxybutyl-(S)-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.24(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 6.90~7.20(m, 4H)

Example 181 : Synthesis of l-(4-fluorophenyl)-(S)-l-methoxy-3-methyl-butyl-(S)-2- carbam

1H NMR(400MHz, CDC1 ₃ ) 81.07(t, J=7.6Hz, 6H), 1.83~1.89(m, IH), 3.24(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 6.92-7.17(m, 4H)

Example 182 : Synthesis of l-(4-fluorophenyl)-(S)-l-methoxyhexyl-(S)-2-carbamate

Ή NMR(400MHz, CDC1 ₃ ) 50.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 3.23(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 6.96~7.19(m, 4H)

Example 183 : Synthesis of l-(2,4-dichlorophenyl)-(S)-l-methoxypropyl-(S)-2- carbamate

1H NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8Hz, 3H), 3.24(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.24~7.30(m, 2H), 7.73(d, J=1.5Hz, IH)

Example 184 : Synthesis of l-(2,4-dichlorophenyl)-(S)-l-methoxybutyl-(S)-2- carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.24(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 7.24~7.30(m, 2H), 7.73(d, J=1.5Hz, IH)

Example 185 : Synthesis of l-(2,4-dichlorophenyl)-(S)-l-methoxy-3-methyl-butyl- (S)-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.07(t, J=7.6Hz, 6H), 1.83~1.89(m, 1H), 3.24(s, 3H), 4.71 (d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 7.24~7.30(m, 2H), 7.73(d, J=1.5Hz, 1H)

Example 186 : Synthesis of l-(2,4-dichlorophenyl)-(S)-l-methoxyhexyl-(S)-2- carbamate

1H NMR(400MHz, CDC1 ₃ ) 50.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 3.24(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 7.24~7.30(m, 2H), 7.73(d, J=1.5Hz, 1H)

Example 187 : Synthesis of l-(2,6-dichlorophenyl)-(S)-l-methoxypropyl-(S)-2- carbamate

Ή NMR(400MHz, CDC1 ₃ ) 51.37(d, J=6.8Hz, 3H), 3.24(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 7.57~7.58(m, 3H)

Example 188 : Synthesis of l-(2,6-dichlorophenyl)-(S)-l-methoxybutyl-(S)-2- carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.24(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 7.54~7.57(m, 3H) Example 189 : Synthesis of l-(2,6-dichlorophenyl)-(S)-l-methoxy-3-methyl-butyl- (S)-2-carbamate

Ή NMR(400MHz, CDC1 ₃ ) 51.07(t, J=7.6Hz, 6H), 1.83~1.89(m, 1H), 3.24(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 7.55~7.57(m, 3H)

Example 190 : Synthesis of l-(2,4-dichlorophenyl)-(S)-l-methoxyhexyl-(S)-2- carba

1H NMR(400MHz, CDC1 ₃ ) 50.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 3.23(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 7.54~7.59(m, 3H)

Example 191 : Synthesis of l-(2,3-dichlorophenyl)-(S)-l-methoxypropyl-(S)-2- carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.37(d, J=6.8Hz, 3H), 3.24(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 7.01~7.14(m, 3H)

Example 192: Synthesis of l-(2-chlorophenyl)-(R)-l-methoxypropyl-(R)-2- carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.37(d, J=6.8 Hz, 3H), 3.24(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 7.26~7.70(m, 4H)

Example 193 : Synthesis of l-(2-chlorophenyl)-l-methoxypropyl-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8 Hz, 3H), 3.24(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 7.26~7.70(m, 4H)

Example 194 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxypropyl-(S)-2- carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.37(d, J=6.8 Hz, 3H), 3.24(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 7.26~7.70(m, 4H)

Example 195 : Synthesis of l-(2-chlorophenyl)-(S)-l-methoxypropyl-(R)-2- carbamate

Ή NMR(400MHz, CDC1 ₃ ) 51.37(d, J=6.8 Hz, 3H), 3.24(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 7.26~7.70(m, 4H) J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 7.26~7.70(m, 4H)

Example 200 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxyhexyl-(R)-2- carbamate

Ή NMR(400MHz, CDC1 ₃ ) 60.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 3.24(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 7.26~7.70(m, 4H)

Example 201 : Synthesis of l-(2-chlorophenyl)-l-methoxyhexyl-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 60.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 3.24(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 7.26~7.70(m, 4H)

Example 202 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxypropyl-(R)-2- methylcarbamate

Ή NMR(400MHz, CDC1 ₃ ) 51.37(d, J=6.8 Hz, 3H), 2.58(s, 3H), 3.24(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 7.26~7.70(m, 4H)

Example 203 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxypropyl-(R)-2- propylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 50.90(t, J=6.8 Hz, 3H), 1.37(d, J=6.8 Hz, 3H), 1.60(m, 2H), 3.18(t, J=7.1Hz, 2H), 3.23(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.26~7.70(m, 4H)

Example 204 : Synthesis of l-(2-chlorophenyI)-(R)-l-thoxypropyl-(R)-2- isopropylcarbamate

Ή NMR(400MHz, CDC1 ₃ ) δ, 1.27(d, J=6.8 Hz, 6H), 1.37(d, J=6.8 Hz, 3H), 3.23(s, 3H), 4.17(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IHH), 7.26~7.70(m, 4H)

Example 205 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxypropyl-(R)-2- cyclopropylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 50.57(m, 2H), 0.82(m, 2H), 1.37(d, J=6.8 Hz, 3H), 2.75(m, IH), 3.24(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.26~7.70(m, 4H)

Example 206 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxypropyI-(R)-2- cyclohexylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 51.11-1.21 (m, 4H), 1.37(d, J=6.8 Hz, 3H), 1.47~1.49(m, 4H), Example 196 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxybutyl-(R)-2- carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.24(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 7.26~7.70(m, 4H)

Example 197 : Synthesis of l-(2-chlorophenyl)-l-methoxybutyl-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 61.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.23(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 7.26~7.70(m, 4H)

Example 198 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxy-3-methyl-butyl-(R)- 2-carbamate

Ή NMR(400MHz, CDC1 ₃ ) 51.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.24(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 7.26~7.70(m, 4H)

Example 199 : Synthesis of l-(2-chlorophenyl)-l-methoxy-3-methyl-butyl-2- carbamate

Ή NMR(400MHz, CDC1 ₃ ) 51.07(t, J=7.6Hz, 6H), 1.83~1.89(m, 1H), 3.24(s, 3H), 4.71 (d,

197 1.74(m, 2H), 3.24(s, 3H), 3.54(m, IH), 4.71 (d, J=6.8, IH), 4.82~4.88(m, IH), 7.26~7.70(m, 4H)

Example 207 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxypropyl-(R)-2- cyclohexylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 51.37(d, J=6.8 Hz, 3H), 3.24(s, 3H), 4.20(m, 2H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.13~7.19(m, 4H), 7.37~7.88(m, 5H)

Example 208 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxypropyl-(R)-2- bicyclo[2,2,l]heptanescarbamate

1H NMR(400MHz, CDC1 ₃ ) 51.33~1.58(m, 9H), 1.75~1.88(m, 2H), 2.06~2.13(m, 2H), 3.22(s, 3H), 3.53(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.13~7.19(m, 4H), 7.37~7.88(m, 5H)

Example 209 : Synthesis of l-(2-fluorophenyl)-(R)-l-methoxypropyl-(R)-2- carbamate

1H NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8 Hz, 3H), 3.23(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.15~7.68(m, 4H)

Example 210 : Synthesis of l-(4-fluorophenyl)-(R)-l-methoxypropyl-(R)-2- carbamate

Ή NMR(400MHz, CDC1 ₃ ) 51.37(d, J=6.8 Hz, 3H), 3.23(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 6.96-7.17(m, 4H)

Example 211 : Synthesis of l-(4-fluorophenyI)-(R)-l-methoxybutyl-(R)-2- carbam

^] H NMR(400MHz, CDC1 ₃ ) 61.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.24(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 6.90~7.20(m, 4H)

Example 212 : Synthesis of l-(4-fluorophenyl)-(R)-l-methoxy-3-methyl-butyl-(R)-2- carbam

1H NMR(400MHz, CDC1 ₃ ) 51.07(t, J=7.6Hz, 6H), 1.83~1.89(m, 1H), 3.23(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 6.92~7.17(m, 4H)

Example 213 : Synthesis of l-(4-fluorophenyl)-(R)-l-methoxyhexyl-(R)-2- carbamate

1H NMR(400MHz, CDC1 ₃ ) 50.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 3.23(s, 3H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 4.82~4.88(m, 1H), 6.96-7.19(m, 4H) Example 214 : Synthesis of l-(2-iodophenyl)-(R)-l-methoxypropyl-(R)-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8 Hz, 3H), 3.24(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 7.13~7.88(m, 4H)

Example 215 : Synthesis of l-(2-iodophenyl)-(R)-l-methoxybutyl-(R)-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 61.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.23(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), , 7.26~7.70(m, 4H)

Example 216 : Synthesis of l-(2-iodophenyl)-(R)-l-methoxy-3-methyl-butyl-(R)-2- carba

1H NMR(400MHz, CDC1 ₃ ) 61.07(d, J=7.6Hz, 3H), 1.83~1.89(m, 1H), 3.24(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 7.26~7.70(m, 4H)

Example 217 : Synthesis of l-(2-iodophenyl)-(R)-l-methoxyhexyl-(R)-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 80.84(t, J=7.0Hz, 3H), 1.20~1.35(m, 4H), 1.36~1.41(m, 1H), 1.59~1.63(m, 1H), 3.30(s, 3H), 4.47(br s, 2H), 4.71(d, J=6.8, lH), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 218 : Synthesis of l-(3-iodophenyl)-(R)-l-methoxypropyl-(R)-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.16(d, J=6.4Hz, 3H), 3.23(s, 3H), 4.54~4.63(m, 4H), 5.04-5.10(m, 1H), 7.09~7.73(m, 4H)

Example 219 : Synthesis of l-(3-iodophenyl)-(R)-l-methoxybutyl-(R)-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.24(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 7.26~7.70(m, 4H)

Example 220 : Synthesis of l-(3-iodophenyl)-(R)-l-methoxy-3-methyl-butyl-(R)-2- carbam

1H NMR(400MHz, CDC1 ₃ ) 51.07(d, J=7.6Hz, 3H), 1.83~1.89(m, 1H), 3.24(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 7.26~7.70(m, 4H)

Example 221 : Synthesis of l-(3-iodophenyl)-(R)-l-methoxyhexyl-(R)-2-carbamate

Ή NMR(400MHz, CDC1 ₃ ) 50.84(t, J=7.0Hz, 3H), 1.20~1.35(m, 4H), 1.36~1.41(m, 1H), 1.59~1.63(m, IH), 3.30(s, 3H), 4.47(br s, 2H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.26~7.70(m, 4H)

Example 222 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxypropyl-(R)-2- methylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8 Hz, 3H), 2.58(s, 3H), 2.24(s, 3H), 4.71 (d, J=6.8, IH), 4.82~4.88(m, IH), 7.26~7.70(m, 4H)

Example 223 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxypropyl-(R)-2- propylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 60.90(t, J=6.8 Hz, 3H), 1.37(d, J=6.8 Hz, 3H), 1.60(m, 2H), 3.18(t, J=7.1Hz, 2H), 3.23(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.26~7.70(m, 4H)

Example 224 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxypropyl-(R)-2- isopropylcarbamate

1H NMR(400MHz, CDC1 ₃ ) δ, 1.27(d, J=6.8 Hz, 6H), 1.37(d, J=6.8 Hz, 3H), 3.24(s, 3H), 4.17(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.26~7.70(m, 4H)

Example 225 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxypropyl-(R)-2- cyclopropylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 50.57(m, 2H), 0.82(m, 2H), 1.37(d, J=6.8 Hz, 3H), 2.75(m, IH), 3.24(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.26~7.70(m, 4H)

Example 226 : Synthesis of l-(2-chlorophenyI)-(R)-l-methoxypropyl-(R)-2- cyclohexylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 61.11-1.21 (m, 4H), 1.37(d, J=6.8 Hz, 3H), 1.47~1.49(m, 4H), 1.74(m, 2H), 3.24(s, 3H), 3.54(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.26~7.70(m, 4H)

Example 227 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxypropyl-(R)-2- cyclohexylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8 Hz, 3H), 3.24(s, 3H), 4.20(m, 2H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.13~7.19(m, 4H), 7.37~7.88(m, 5H)

Example 228 : Synthesis of l-(2-chlorophenyl)-(R)-l-methoxypropyl-(R)-2- bicyclo[2,2,l]heptanescarbamate

1H NMR(400MHz, CDC1 ₃ ) 51.33~1.58(m, 9H), 1.75~1.88(m, 2H), 2.06-2.13(m, 2H), 3H), 3.53(m, IH), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.13~7.19(m, 4H), 7.37~7.88(m, 5H)

Example 229 : Synthesis of l-(2,4-dichIorophenyl)-(R)-l-methoxypropyl-(R)-2-

1H NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8Hz, 3H), 3.24(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.24~7.30(m, 2H), 7.73(d, J=1.5Hz, IH)

Example 230 : Synthesis of l-(2,6-dichlorophenyl)-(R)-l-methoxypropyl-(R)-2- carbamate

1H NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8Hz, 3H), 3.24(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.57~7.58(m, 3H)

Example 231 : Synthesis of l-(2,3-dichlorophenyl)-(R)-l-methoxypropyl-(R)-2- carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.37(d, J=6.8Hz, 3H), 3.24(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.01-7.14(m, 3H)

Example 232 : Synthesis of l-(2,4-dichlorophenyl)-(R)-l-methoxybutyl-(R)-2- carbamate

Ή NMR(400MHz, CDC1 ₃ ) 61.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.24(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 7.24~7.30(m, 2H), 7.73(d, J=1.5Hz, IH)

Example 233 : Synthesis of l-(2,6-dichlorophenyI)-(R)-l-methoxybutyl-(R)-2- carbam

Ή NMR(400MHz, CDC1 ₃ ) 51.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.24(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 7.54~7.57(m, 3H)

Example 234 : Synthesis of l-(2,4-dichlorophenyl)-(R)-l-methoxy-3-methyl-butyl- (R)-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.07(t, J=7.6Hz, 6H), 1.83~1.89(m, IH), 3.24(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 7.24~7.30(m, 2H), 7.73(d, J=1.5Hz, IH)

Example 235 : Synthesis of l-(2,6-dichlorophenyl)-(R)-l-methoxy-3-methyl-butyl- (R)-2-carbamate

Ή NMR(400MHz, CDC1 ₃ ) 51.07(t, J=7.6Hz, 6H), 1.83~1.89(m, IH), 3.24(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 7.55~7.57(m, 3H) Example 236 : Synthesis of l-(2,4-dichlorophenyl)-(R)-l-methoxyhexyl-(R)-2- carba

Ή NMR(400MHz, CDC1 ₃ ) 50.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 3.24(s, 3H), 4.7 l(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 7.24~7.30(m, 2H), 7.73(d, J=1.5Hz, IH)

Example 237 : Synthesis of l-(2,4-dichlorophenyl)-(R)-l-methoxyhexyl-(R)-2- carba

Ή NMR(400MHz, CDC1 ₃ ) 50.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 3.23(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 7.54~7.59(m, 3H)

Example 238 : Synthesis of l-(2,4-dichlorophenyl)-l-methoxypropyl-2-carbamate

1H NMR(400MHz, CDCI3) 61.37(d, J=6.8Hz, 3H), 3.23(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.24~7.30(m, 2H), 7.73(d, J=1.5Hz, IH)

Example 239 : Synthesis of l-(2,6-dichlorophenyl)-l-methoxypropyl-2-carbamate

Ή NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8Hz, 3H), 3.24(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.57~7.58(m, 3H)

Example 240 : Synthesis of l-(2,3-dichlorophenyl)-l-methoxypropyl-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8Hz, 3H), 3.24(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.01~7.14(m, 3H)

Example 241 : Synthesis of l-(2,4-dichlorophenyl)-l-methoxybutyl-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 61.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.23(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 7.24~7.30(m, 2H), 7.73(d, J=1.5Hz, IH)

Example 242 : Synthesis of l-(2,6-dichlorophenyl)-l-methoxybutyf-2-carbamate

Ή NMR(400MHz, CDCI3) 51.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 3.24(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 7.54~7.57(m, 3H)

Example 243 : Synthesis of l-(2,4-dichlorophenyl)-l-methoxy-3-methyl-butyl-2- carba

1H NMR(400MHz, CDC1 ₃ ) 51.07(t, J=7.6Hz, 6H), 1.83~1.89(m, IH), 3.24(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 7.24~7.30(m, 2H), 7.73(d, J=1.5Hz, IH)

Example 244 : Synthesis of l-(2,6-dichlorophenyl)-l-methoxy-3-methyl-butyl-2- carb

1H NMR(400MHz, CDC1 ₃ ) 51.07(t, J=7.6Hz, 6H), 1.83~1.89(m, IH), 3.24(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 7.55~7.57(m, 3H)

Example 245 : Synthesis of l-(2,4-dichlorophenyl)-l-methoxyhexyl-2-carbamate

Ή NMR(400MHz, CDC1 ₃ ) 50.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 3.24(s, 3H), 4.71 (d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 7.24~7.30(m, 2H), 7.73(d, J=1.5Hz, IH)

Example 246 : Synthesis of l-(2,4-dichlorophenyl)-l-methoxyhexyl-2-carbamate

1H NMR(400MHz, CDCI ₃ ) 60.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 3.24(s, 3H), 4.71(d, J=6.8, IH), 4.73(br s, 2H), 4.82~4.88(m, IH), 7.54~7.59(m, 3H)

Example 247 : Synthesis of l-(2-chlorophenyl)-(S)-l-carbamoyloxypropyI-(S)-2- carbamate

l-(2-chlorophenyl)-l-hydroxypropyl-l-carbamate(Preparation Example 103, 8g), tetrahydrofuran (THF), and carbonyldiimidazole (CDI, 1.5eq, 9.1g) were put into a flask and stirred at the room temperature. After approximately 3 hours, ammonia solution (NH OH, 3eq, 4.4ml) was added thereto. When the reaction was completed, the obtained product was washed with 1M HC1 solution and ethylacetate (EA). The separated organic layer was dehydrated with anhydrous MgS0 ₄ (Magnesium sulfate), filtrated, and concented under reduced pressure. The concentrated residue was purified by a silica gel column chromatography, to obtain the title compound.

Ή NMR(400MHz, DMSO-i¾ 51.12(d, J = 6.4Hz, 3H), 4.97~5.03(m, 1H), 5.91(d, J = 5.2Hz, 1H), 6.31~6.92(m, 4H), 7.30~7.42(m, 4H)

According to the method described in Example 247, the following compounds of Examples 248 to 256 were prepared:

Example 248 : Synthesis of l-(2-chlorophenyl)-(S)-l-carbamoyloxypropyl-(S)-2- methylcarbamate

1H NMR(400MHz, CDC1 ₃ ) 51.40(d, J=6.0Hz, 3H), 2.74(s, 3H), 4.71(d, J=6.4Hz, 1H), 4.80~4.85(m, 1H), 6.30~6.90(br s, 3H), 7.28~7.43(m, 4H)

Example 249 : Synthesis of l-(2-chlorophenyl)-(S)-l-carbamoyloxypropyl-(S)-2- propylcarbamate

Ή NMR(400MHz, CDCI3) 50.96(t, J=6.4Hz, 3H), 1.40(d, J=6.0Hz, 3H), 1.55~1.60(m, 2H), 2.96(t, J=6.0Hz, 2H), 4.71(d, J=6.0Hz, 1H), 4.82~4.88(m, 1H), 6.76(br s, 3H), 7.07-7.21 (m, 4H)

Example 250 : Synthesis of l-(2-chlorophenyl)-(R)-2-carbamoyloxypropyl-(R)-l- carbamate(2)

1H NMR(400MHz, DMSO-<¾) 61.12(d, J = 6.4Hz, 3H), 4.97~5.04(m, 1H), 5.92(d, J = 5.2Hz, 1H), 6.25~6.83(m, 4H), 7.30~7.44(m, 4H)

Example 251 : Synthesis of l-(2-chlorophenyl)-2-carbamoyloxypropyl-l- carbamate(3)

Ή NMR(400MHz, DMSO- ₆ ) 5l .l2(d, J = 6.4Hz, 3H), 4.97~5.03(m, 1H), 5.91(d, J = 5.2Hz, 1H), 6.31~6.92(m, 4H), 7.30~7.42(m, 4H)

Example 252 : Synthesis of l-(2-chlorophenyl)-(S)-l-carbamoyloxybutyl-(S)-2- carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.04(t, J=7.6Hz, 3H), 1.60~1.71(m, 2H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 5.82~5.88(m, 1H), 7.26~7.70(m, 4H)

Example 253 : Synthesis of l-(2-chlorophenyl)-(S)-l-carbamoyloxy-3-methyl-butyl- (S)-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 61.07(t, J=7.6Hz, 6H), 1.83~1.89(m, 1H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 5.80~5.88(m, 1H), 7.26~7.70(m, 4H)

Example 254 : Synthesis of l-(2-chlorophenyl)-(S)-l-carbamoyloxyhexyl-(S)-2- carb

Ή NMR(400MHz, CDC1 ₃ ) 60.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 4.71(d, J=6.8, 1H), 4.73(br s, 2H), 5.82~5.88(m, 1H), 7.26~7.70(m, 4H)

Example 255 : Synthesis of l-(2-fluorophenyl)-(S)-l-carbamoyloxypropyl-(S)-2- carbamate

1H NMR(400MHz, DMSO-<¾) 61.37(d, J=6.8 Hz, 3H), 4.71 (d, J=6.8, 1H), 5.82~5.88(m 1H), 7.15~7.68(m, 4H)

Example 256 : Synthesis of l-(2-fluorophenyl)-(S)-l-carbamoyloxybutyl-(S)-2-

1H NMR(400MHz, CDC1 ₃ ) 51.02(t, J=7.2Hz, 3H), 1.60~1.71(m, 2H), 4.71 (d, J=6.8Hz, 1H), 4.73(br s, 2H), 5.82~5.88(m, 1H), 6.09~7.17(m, 4H)

Example 257 : Synthesis of l-(2-fluorophenyl)-(S)-l-carbamoyloxy-3-methyl-butyl- (S)-2-carbamate

Ή NMR(400MHz, CDC1 ₃ ) 51.07(t, J=7.6Hz, 6H), 1.83~1.89(m, 1H), 4.71(d, J=6.8Hz, 1H), 4.73(br s, 2H), 5.80~5.88(m, 1H), 6.10~7.20(m, 4H)

Example 258 : Synthesis of l-(2-fluorophenyl)-(S)-l-carbamoyloxyhexyl-(S)-2- carbamate

1H NMR(400MHz, CDC1 ₃ ) 60.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 4.71(d, J=6.8Hz, 1H), 4.73(br s, 2H), 5.82~5.88(m, 1H), 7.16~7.69(m, 4H)

Example 259 : Synthesis of l-(2-iodophenyl)-(S)-l-carbamoyloxypropyl-(S)-2- carba

^! H NMR(400MHz, DMSO- ¾) 61.37(d, J=6.8 Hz, 3H), 4.71(d, J=6.8Hz, 1H), 4.82~4.88(m, 1H), 7.13~7.88(m, 4H)

Synthesis of l-(2-iodophenyl)-(S)-l-carbamoyloxybutyl-(S)-2- carb

1H NMR(400MHz, CDC1 ₃ ) 61.02(t, J=7.2Hz, 3H), 1.60~1.71(m, 2H), 4.71(d, J=6.8Hz, 1H), 4.73(br s, 2H), 5.82~5.88(m, 1H), 6.96~7.57(m, 4H)

Example 261 : Synthesis of l-(2-iodophenyl)-(S)-l-carbamoyloxy-3-methyl-butyl- (S)-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.07(t, J=7.6Hz, 6H), 1.83~1.89(m, 1H), 4.71(d, J=6.8Hz, 1H), 4.73(br s, 2H), 5.80~5.88(m, 1H), 6.98~7.61(m, 4H)

Example 262 Synthesis of l-(2-iodophenyl)-(S)-l-carbamoyloxyhexyl-(S)-2- carbam

1H NMR(400MHz, CDC1 ₃ ) 60.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 4.71 (d, J=6.8Hz, 1H), 4.73(br s, 2H), 5.82~5.88(m, 1H), 6.95-7.6 l(m, 4H)

Example 263 : Synthesis of l-(2,4-dichlorophenyl)-(S)-l-carbamoyloxypropyl-(S)-2- carb

1H NMR(400MHz, DMSO- ₆ ) 61.37(d, J=6.8 Hz, 3H), 4.71(d, J=6.8Hz, 4.82~4.88(m, 1H), 7.07~7.21(m, 3H)

Example 264 : Synthesis of l-(2,4-dichlorophenyl)-(S)-l-carbamoyloxybutyl-(S)-2- carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.02(t, J=7.2Hz, 3H), 1.60~1.71(m, 2H), 4.71(d, J=6.8Hz, 1H), 4.73(br s, 2H), 5.82-5.88(m, 1H), 7.05-7.1 (m, 3H)

Example 265 : Synthesis of l-(2,4-dichlorophenyl)-(S)-l-carbamoyloxy-3-methyl- butyl-(S -2-carbamate

Ή NMR(400MHz, CDC1 ₃ ) 51.07(t, J=7.6Hz, 6H), 1.83-1.89(m, 1H), 4.71(d, J=6.8Hz, 1H), 4.73(br s, 2H), 5.80~5.88(m, 1H), 7.02-7.17(m, 3H)

Example 266 : Synthesis of l-(2,4-dichlorophenyl)-(S)-l-carbamoyloxyhexyl-(S)-2- carb

Ή NMR(400MHz, CDC1 ₃ ) 50.90(t, J=7.6Hz, 3H), 1.35-1.65(m, 6H), 4.71 (d, J=6.8Hz, , 4.73(br s, 2H), 5.82~5.88(m, 1H), 7.08~7.22(m, 3H)

Example 267 : Synthesis of l-(2,6-dichlorophenyl)-(S)-l-carbamoyloxypropyl-(S)-2- carbamate

1H NMR(400MHz, DMSO-J*) 61.37(d, J=6.8 Hz, 3H), 4.71(d, J=6.8Hz, 1H), 4.82~4.88(m, 1H), 7.07~7.11(m, 3H)

Example 268 : Synthesis of l-(2,6-dichlorophenyl)-(S)-l-carbamoyIoxybutyl-(S)-2- carba

Ή NMR(400MHz, CDC1 ₃ ) 51.02(t, J=7.2Hz, 3H), 1.60~1.71(m, 2H), 4.71(d, J=6.8Hz, 1H), 4.73(br s, 2H), 5.82~5.88(m, 1H), 7.05-7.10(m, 3H)

Example 269 : Synthesis of l-(2,6-dichlorophenyl)-(S)-l-carbamoyloxy-3-methyl- butyl-(S -2-carbamate

Ή NMR(400MHz, CDC1 ₃ ) 51.07(t, J=7.6Hz, 6H), 1.83~1.89(m, 1H), 4.71(d, J=6.8Hz, 1H), 4.73(br s, 2H), 5.80~5.88(m, 1H), 7.02~7.08(m, 3H)

Example 270 : Synthesis of l-(2,6-dichlorophenyl)-(S)-l-carbamoyloxyhexyl-(S)-2- carbamate

1H NMR(400MHz, CDC1 ₃ ) 50.90(t, J=7.6Hz, 3H), 1.35~1.65(m, 6H), 4.71(d, J=6.8Hz, 1H), 4.73(br s, 2H), 5.82~5.88(m, 1H), 7.05-7.12(m, 3H)

Example 271 : Synthesis of l-(2,6-difluorophenyl)-(S)-l-methoxymethoxypropyl- (S)-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 51.37(d, J=6.8Hz, 3H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 6.67-7.15(m, 3H)

Example 272 : Synthesis of l-(2,5-dichlorophenyl)-(S)-l-methoxymethoxypropyl- (S)-2-carbamate

Ή NMR(400MHz, CDC1 ₃ ) 51.37(d, J=6.8Hz, 3H), 3.30(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.13~7.26(m, 3H)

Example 273 : Synthesis of l-(2,5-dichlorophenyl)-(R)-l-methoxymethoxypropyl- (R)-2-carbamate

1H NMR(400MHz, CDC1 ₃ ) 61.37(d, J=6.8Hz, 3H), 3.30(s, 3H), 4.7 l (d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.13~7.26(m, 3H)

Example 274 : Synthesis of l-(2-chlorophenyl)-(S)-2-methoxymethoxypropyl-(S)-l- carbamate

1H NMR(400MHz, CDC1 ₃ ) 61.21(d, J=6.8Hz, 3H), 3.24(s, 3H), 3.94~4.05(m, 1H), 5.45(s, 2H), 5.56(d, J=6.8Hz, 1H), 7.07~7.20(m, 4H)

Example 275 : Synthesis of l-(2-chlorophenyl)-(S)-2-methoxypropyl-(S)-l- carbamate

1H NMR(400MHz, CDC1 ₃ ) 81.23(d, J=6.4Hz, 3H), 3.22(s, 3H), 3.99(m, 1H), 5.52(d, J=6.4Hz, 1H), 7.07-7.2 l (m, 4H)

Example 276 : Synthesis of l-(2-chlorophenyl)-(S)-l-methoxymethoxyethyl-2- carbamate

1H NMR(400MHz, DMSO-i/ ₆ ) 53.30(s, 3H), 4.71(d, J=6.8, 1H), 4.82~4.88(m, 1H), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 277 : Synthesis of l-(2-fluorophenyl)-(S)-l-methoxymethoxyethyl-2- carbamate

1H NMR(400MHz, CDC1 ₃ ) 63.30(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 5.45(s, 2H), 7.26~7.70(m, 4H)

Example 278 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxymethoxyethyl-2- carbamate

1H NMR(400MHz, DMSO-i/ ₆ ) 53.26(s, 3H), 3.94~4.09(m, IH), 4.47(d, J=6.8Hz, IH), 4.60(d, J=6.8Hz, IH), 4.97(m, IH), 6.55(br 2H), 7.07~7.87(m, 4H)

Example 279 : Synthesis of l-(2-chlorophenyl)-(S)-l-methoxyethyl-2-carbamate

1H NMR(400MHz, DMSO-i¾ 53.27(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 6.47~6.63(br 2H), 7.26~7.70(m, 4H)

Example 280 : Synthesis of l-(2-fluorophenyl)-(S)-l-methoxyethyl-2-carbamate

1H NMR(400MHz, OMSO-d ₆ ) 53.29(s, 3H), 4.71(d, J=6.8, IH), 4.82~4.88(m, IH), 7.26~7.70(m, 4H)

Example 281 : Synthesis of l-(2-iodophenyl)-(S)-l-methoxethyl-2-carbamate

1H NMR(400MHz, DMSO-</ ₆ ) 53.28(s, 3H), 3.94~4.09(m, 1H), 4.97(m, 1H), 7.07~7.87(m, 4H)

[Animal Testing Examples]

For testing, male mice (ICR) were purchased from ORIENT BIO INC. (Korea), divided into several groups with 6 mice in each group, and were adapted for 4-5 days. The mice having the weight ranging from 19g to 26g were employed for the test. The pharmacological effect of the test compounds on muscle relaxation was evaluated by Rotarod test, grip strength test, and muscular force (wire hang) test. All mice were adapted to the test environment at one hour before starting the tests. The pharmacological effects of all the test compounds were evaluated by administration through peritoneal cavity of the mice (10 ul/g, bw).

Experimental Example 1: Measurement of muscle relaxation activity by residence time on a rotarod rotating at a fixed speed

All the mice to be tested were preliminarily trained for 5 minutes on a rod rotating at the rate of 15 revolutions per a minute. The mice that could not remain on the rod without falling off therefrom for a minimum of 2 minutes were excluded from this testing. After the training, all the mice were allowed to rest for 45-60 minutes. Before the administration of the test compounds, the mice were subjected to a further training for one minute on the rod rotating under the same condition, where the mice falling off from the rod were excluded from this experimentation. All the test compounds were intraperitoneally administered (10 ul/g, bw) to the mice at 15 minutes, 30 minutes, 1 hour, and 2 hours prior to the testing, and the median effective concentration (ED50) was determined at the time(generally 15 min, 30min or 60min) that the comounds exhibit their maximum pharmacological effect. In case a mouse stays on the rod until the test is finished, the time was recorded as 10 minutes. As test time for evaluation, a maximum of 10 minutes was applied. The obtained results were shown in following Table 2. This experimentation was conducted according to the method described in the reference, 'Yasuda et al. (2005) Antipyretic, analgesic and muscle relaxant activities of Pueraria isoflavonoids and their metabolites from Pueraria lobata Ohwi - a traditional Chinese drug. Biol. Pharm. Bull. 28: 1224-1228'.

Experimental Example 2: Measurement of muscle relaxation activity by grip strenth

A grip strength test using the test animals' forelimbs was performed using an instrument equipped with triangle ring and designed so as to easily grip with the forelimbs of experimental animals, manufactured from Ugo Basile Inc.(Ugo Basile, Model47106, Italy). The test was conducted before and after administration of the compounds to evaluate the effects thereof. All the test compounds were intraperitoneally administered (10 ul/g, bw) at 15 minutes, 30 minutes, 1 hour, and 2 hours before test, and the median effective concentration (ED50) was determined at the time(generally 15 min, 30min or 60min) that the compounds exhibits therir maximum pharmacological effect. The mouse was made to grip the rod with its forelimbs, and its tail was pulled, where the force at which the mouse detached from the rod was recorded. The instrument indicated the force in grams. All of the mice were given 3 opportunities for test, and the 3 highest values among the test opportunities were selected and the mean value was used as the test result. The obtained results are shown in Table 2. This experimentation was conducted according to the method described in the reference, 'Nevins et al. (1993) Quantitative grip strength assessment as a means of evaluating muscle relaxation in mice. Psychopharmacol. 110: 92-96'.

Experimental Example 3: Measurement of muscle relaxation activity by wire hang

This experimentation was conducted using a metal wire of 30cm in length, which was suspended between two pillars at a height of about 40cm from the bottom covered with a soft pad. All the test compounds were administered to the mice through peritoneal cavity (10 ul/g, bw) at 15 minutes, 30 minutes, 1 hour, and 2 hours prior to the testing, and the median effective concentration (ED50) was determined at the time that the compound exhibits the maximum pharmacological effect. Each mouse was made to grip the wire using two forelimbs, and the elapse time before the mouse fell off from the wire to the pad on the bottom was recorded in seconds. Each mouse was given 5 opportunities for this test at an interval of 2 minutes period.

The highest 3 records among the test opportunities were selected and the mean value was used as the test result. The obtained results are shown in Table 2. This experimentation was was conducted according to the method described in the reference, 'Jacqueline N. Crawley (1999) Behavioral phenotyping of transgenic and knockout mice: experimental design and evaluation of general health, sensory functions, motor abilities, and specific behavioral tests. Brain Res. 835: 18-26'.

[Results]

The results of muscle relaxation activity of the phenyl alkyl carbamate derivative compounds measured in above Experimental Examples 1 to 3 are shown in following Table 3. In the Table 3, the ED50 was represented by the concentration where the compound shows the 50% of muscle relaxation activity compared to the vehicle only (100%).

(Table 3) Results of the measurements of muscle relaxation activity of the phenyl alkyl carbamate derivatives

I = Fixed 15 r.p.m. Rotarod (constantly rotating ratarod test; Experimental Example 1),

II = Grip strength (Experimental Example 2),

III = Wire hang (Experimental Example 3)

a = the concentration administered and effect(%, peak time(hr)) compared to that of control treated with vehicle only

Control: administered with vehicle only (Vehicle : 20% Tween 80)