Title:
METHOD FOR PRODUCING OPTICALLY ACTIVE 4-AMINO-3-(3,4-DICHLOROPHENYL)BUTAN-1-OL AND INTERMEDIATE THEREFOR
Document Type and Number:
WIPO Patent Application WO/2009/102043
Kind Code:
A1
Abstract:
Disclosed is a method for producing an optically active 4-amino-3-(3,4-dichlorophenyl)butan-1-ol, wherein an optically active 3-(3,4-dichlorophenyl)-4-nitrobutanal is obtained by reacting 3-(3,4-dichlorophenyl)acrylaldehyde with nitromethane in the presence of an optically active pyrrolidine compound, then an optically active 3-(3,4-dichlorophenyl)-4-nitrobutan-1-ol is obtained by reducing a formyl group of the optically active 3-(3,4-dichlorophenyl)-4-nitrobutanal, and then a nitro group of the optically active 3-(3,4-dichlorophenyl)-4-nitrobutan-1-ol is reduced.
Inventors:
HAYASHI YUJIRO (JP)
IKEMOTO TETSUYA (JP)
YASUOKA JUNICHI (JP)
IKEMOTO TETSUYA (JP)
YASUOKA JUNICHI (JP)
Application Number:
PCT/JP2009/052446
Publication Date:
August 20, 2009
Filing Date:
February 06, 2009
Export Citation:
Assignee:
SUMITOMO CHEMICAL CO (JP)
HAYASHI YUJIRO (JP)
IKEMOTO TETSUYA (JP)
YASUOKA JUNICHI (JP)
HAYASHI YUJIRO (JP)
IKEMOTO TETSUYA (JP)
YASUOKA JUNICHI (JP)
International Classes:
C07C213/02; C07C205/26; C07C205/44; C07C215/28; C07B53/00; C07B61/00
Foreign References:
| JPH08176108A | 1996-07-09 | |||
| JPS291823B1 | ||||
| JP2004352708A | 2004-12-16 |
Other References:
HIROAKI GOTOH ET AL.: "Diphenylprolinol Silyl Ether as Catalyst of an Asymmetric, Catalytic, and Direct Michael Reaction of Nitroalkanes with a, beta-Unsaturated Aldehydes", ORGANIC LETTERS, vol. 9, no. 25, 2007, pages 5307 - 5309
SHECHTER H. ET AL.: "Addition Reactions of Nitroalkanes with Acrolein and Methyl Vinyl Ketone. Selective Reduction of Nitrocarbonyl Compounds to Nitrocarbinols", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 74, 1952, pages 3664 - 3668
RUSSELL G.A. ET AL.: "Synthesis of Nitrocyclopropanes by Cyclization of y-Chloro y-nitro Carboxylic Esters and Derivatives", JOURNAL OF ORGANIC CHEMISTRY, vol. 44, no. 8, 1979, pages 1195 - 1199
CAMPS P. ET AL.: "Synthesis of both enantiomers of baclofen using (R)- and (S)- N-phenylpantolactam as chiral auxiliaries, Tetrahedron", ASYMMETRY, vol. 15, 2004, pages 2039 - 2044
SHECHTER H. ET AL.: "Addition Reactions of Nitroalkanes with Acrolein and Methyl Vinyl Ketone. Selective Reduction of Nitrocarbonyl Compounds to Nitrocarbinols", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 74, 1952, pages 3664 - 3668
RUSSELL G.A. ET AL.: "Synthesis of Nitrocyclopropanes by Cyclization of y-Chloro y-nitro Carboxylic Esters and Derivatives", JOURNAL OF ORGANIC CHEMISTRY, vol. 44, no. 8, 1979, pages 1195 - 1199
CAMPS P. ET AL.: "Synthesis of both enantiomers of baclofen using (R)- and (S)- N-phenylpantolactam as chiral auxiliaries, Tetrahedron", ASYMMETRY, vol. 15, 2004, pages 2039 - 2044
Attorney, Agent or Firm:
NAKAYAMA, Tohru et al. (Limited5-33, Kitahama 4-chome, Chuo-k, Osaka-shi Osaka 50, JP)
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