Title:
PROCESS FOR PRODUCING CYCLIC ACETAL FORM OF 3-OXOCYCLOPENTANE-1-CARBOXYLIC ACID
Document Type and Number:
WIPO Patent Application WO/2006/120755
Kind Code:
A1
Abstract:
Provided is a process for producing a cyclic acetal form of 3-oxocyclopentane-1-carboxylic acid more efficiently and industrially advantageously. The process for producing a cyclic acetal form of 3-oxocyclopentane-1-carboxylic acid represented by the general formula (V) is characterized by reacting 3-oxocyclopentane-1-carboxylic acid represented by the general formula (I) with a diol compound represented by the general formula (II) in the presence of an acid catalyst to obtain a mixture of a cyclic acetal monoester derivative and a cyclic acetal diester derivative, and then hydrolyzing the mixture under basic conditions. (I) (II) (V) (In the formulae, R1, R2, R3, R4, R5, R6 and R7 each represents a hydrogen atom, an alkyl group which may have a substituent or an aryl group which may have a substituent; R8, R9, R10, R11, R12 and R13 each represents a hydrogen atom, an alkyl group or an aryl group which may have a substituent, or arbitrary two of them may form a ring together with the carbon atom to which they are linked; and n represents 0 or 1.)
Inventors:
SUGIOKA TAKASHI (JP)
Application Number:
PCT/JP2005/008831
Publication Date:
November 16, 2006
Filing Date:
May 10, 2005
Export Citation:
Assignee:
KURARAY CO (JP)
SUGIOKA TAKASHI (JP)
SUGIOKA TAKASHI (JP)
International Classes:
C07D319/08
Foreign References:
| JP2005272376A | 2005-10-06 | |||
| JPH07509492A | 1995-10-19 | |||
| DE4312832C1 | 1994-10-20 | |||
| US4272437A | 1981-06-09 |
Other References:
SUNG SY ET AL: "Improved Synthesis od (RS)-3-Oxocyclopentanecarboxylic Acid: Characterization of the Intermediates.", PHARMAZIE., vol. 53, no. 8, 1998, pages 521 - 524, XP002992978
HUGHES RE ET AL: "Three-Carbon Annulation. Formation of Five-Membered Rings from Olefins via Diels-Alder Reactions.", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY., vol. 99, no. 16, 1977, pages 5508 - 5510, XP002992979
GAIS HJ ET AL: "Enzyme-Catalyzed Asymmetric Synthesis 8. Enantioselectivity of Pig Liver Esterase Catalyzed Hydrolases of 4-Substituted Meso Cyclopentane 1,2-Diesters.", JOURNAL OF THE ORGANIC CHEMISTRY., vol. 54, no. 21, 1989, pages 5115 - 5122, XP002211112
HUGHES RE ET AL: "Three-Carbon Annulation. Formation of Five-Membered Rings from Olefins via Diels-Alder Reactions.", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY., vol. 99, no. 16, 1977, pages 5508 - 5510, XP002992979
GAIS HJ ET AL: "Enzyme-Catalyzed Asymmetric Synthesis 8. Enantioselectivity of Pig Liver Esterase Catalyzed Hydrolases of 4-Substituted Meso Cyclopentane 1,2-Diesters.", JOURNAL OF THE ORGANIC CHEMISTRY., vol. 54, no. 21, 1989, pages 5115 - 5122, XP002211112
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