Title:
METHOD FOR PRODUCING OPTICALLY ACTIVE (R)- OR (S)-PIPERIDINE-3-CARBOXYLIC ACID COMPOUND AND (S)- OR (R)-PIPERIDINE-3-CARBOXYLIC ACID ALKYL ESTER COMPOUND
Document Type and Number:
WIPO Patent Application WO/2008/072764
Kind Code:
A1
Abstract:
Disclosed is a method for producing an optically active piperidine-3-carboxylic acid compound and an optically active piperidine-3-carboxylic acid alkyl ester compound, wherein one enantiomer of a piperidine-3-carboxylic acid alkyl ester compound as a racemic mixture represented by the general formula (I) is selectively hydrolyzed in the presence of a hydrolytic enzyme. This method is characterized in that an optically active (R)- or (S)-piperidine-3-carboxylic acid compound represented by the general formula (II) is produced during a reaction and precipitated substantially as a solid in an organic solvent, which substantially dissolves optically active piperidine-3-carboxylic acid ester compounds and does not substantially dissolve optically active piperidine-3-carboxylic acid compounds to be produced, while obtaining an unreacted optically active (S)- or (R)-piperidine-3-carboxylic acid alkyl ester compound represented by the general formula (III) in a state substantially dissolved in the solvent.
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Inventors:
YAMAMOTO YASUHITO
WATANABE YOSHIYUKI
KONEGAWA TADAYOSHI
MIYATA HIROYUKI
WATANABE YOSHIYUKI
KONEGAWA TADAYOSHI
MIYATA HIROYUKI
Application Number:
PCT/JP2007/074234
Publication Date:
June 19, 2008
Filing Date:
December 17, 2007
Export Citation:
Assignee:
UBE INDUSTRIES (JP)
YAMAMOTO YASUHITO
WATANABE YOSHIYUKI
KONEGAWA TADAYOSHI
MIYATA HIROYUKI
YAMAMOTO YASUHITO
WATANABE YOSHIYUKI
KONEGAWA TADAYOSHI
MIYATA HIROYUKI
International Classes:
C12P41/00; C12P17/12
Other References:
TOONE E.J. ET AL.: "Enzymes in organic synthesis. 40. Evaluation of the enantioselective of the pig liver esterase catalyzed hydrolyses of racemic piperidine carboxylic acid esters", CAN. J. CHEM., vol. 65, no. 12, 1987, pages 2722 - 2726
WIFFEN J.W. ET AL.: "Collaboration on Chirals", MANUF. CHEM., vol. 77, no. 4, April 2006 (2006-04-01), pages 34 - 35
SOLARES L.F. ET AL.: "Biocatalytic preparation of enantioenriched 3,4-dihydroxypiperidines and theoretical study of Candida antarctica lipase B enantioselectivity", TETRAHEDRON, vol. 62, no. 14, April 2006 (2006-04-01), pages 3284 - 3291, XP025001746, DOI: doi:10.1016/j.tet.2006.01.061
KONEGAWA T. ET AL.: "Koso o Mochiita Kogaku Kassei beta-amino acid Rui no Gosei", CSJ: THE CHEMICAL SOCIETY OF JAPAN KOEN YOKOSHU, vol. 84, no. 2, 2004, pages 1229 + ABSTR. NO. 3K1-25
WIFFEN J.W. ET AL.: "Collaboration on Chirals", MANUF. CHEM., vol. 77, no. 4, April 2006 (2006-04-01), pages 34 - 35
SOLARES L.F. ET AL.: "Biocatalytic preparation of enantioenriched 3,4-dihydroxypiperidines and theoretical study of Candida antarctica lipase B enantioselectivity", TETRAHEDRON, vol. 62, no. 14, April 2006 (2006-04-01), pages 3284 - 3291, XP025001746, DOI: doi:10.1016/j.tet.2006.01.061
KONEGAWA T. ET AL.: "Koso o Mochiita Kogaku Kassei beta-amino acid Rui no Gosei", CSJ: THE CHEMICAL SOCIETY OF JAPAN KOEN YOKOSHU, vol. 84, no. 2, 2004, pages 1229 + ABSTR. NO. 3K1-25
Attorney, Agent or Firm:
TSUKUNI, Hajime (22-12 Toranomon 1-chom, Minato-ku Tokyo 01, JP)
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