Title:
PROCESSES FOR PRODUCING OPTICALLY ACTIVE 1-SUBSTITUTED 2-METHYLPYRROLIDINE AND INTERMEDIATE THEREFOR
Document Type and Number:
WIPO Patent Application WO/2005/073388
Kind Code:
A1
Abstract:
A process for producing an optically active 1,4-pentanediol which comprises asymmetrically reducing 5-hydroxy-2-pentanone, which is easily available at low cost. Also provided is a process for producing an optically active 1-substituted 2-methylpyrrolidine which comprises sulfonylating the optically active 1,4-pentanediol to convert it to an optically active sulfonate compound and subsequently reacting the compound with an amine. By these processes, an optically active 1,4-pentanediol useful as an intermediate for medicines and an intermediate for agricultural chemicals and an optically active 1-substituted 2-methylpyrrolidine can be simply produced from an inexpensive starting material.
Inventors:
NISHIYAMA AKIRA (JP)
TAOKA NAOAKI (JP)
KISHIMOTO NARUMI (JP)
NAGASHIMA NOBUO (JP)
TAOKA NAOAKI (JP)
KISHIMOTO NARUMI (JP)
NAGASHIMA NOBUO (JP)
Application Number:
PCT/JP2005/000575
Publication Date:
August 11, 2005
Filing Date:
January 19, 2005
Export Citation:
Assignee:
KANEKA CORP (JP)
NISHIYAMA AKIRA (JP)
TAOKA NAOAKI (JP)
KISHIMOTO NARUMI (JP)
NAGASHIMA NOBUO (JP)
NISHIYAMA AKIRA (JP)
TAOKA NAOAKI (JP)
KISHIMOTO NARUMI (JP)
NAGASHIMA NOBUO (JP)
International Classes:
C07C303/28; C12P7/18; C12P11/00; C12P17/10; C07C309/66; C12N15/53; (IPC1-7): C12P7/18; C12P17/10
Foreign References:
| JPS4955629A | 1974-05-30 |
Other References:
WHITNEY T.A. ET AL: "Asymmetric Synthesis via Lithium Chelates", ADVANCES IN CHEMISTRY SERIES, vol. 130, 1974, pages 270 - 280, XP002988253
WHITNEY T.A. ET AL: "Asymmetric synthesis via lithium chelates", POLYMER REPRINTS, vol. 13, no. 2, 1972, pages 688 - 692, XP002988254
LETUNOVA A.B. ET AL: "Preparation of gama-acetopropyl alcohol from gama-butyrolactone", KHIMIKO-FARMATSEVTICHESKII ZHURNAL, vol. 11, no. 12, 1977, pages 121 - 123, XP002988255
KIM ET AL: "The efficient resolution of protected diols and hydroxy aldehydes by lipases : Steric auxiliary approach and aynthetic applications.", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 6, no. 1, 1996, pages 71 - 76, XP004135126
WERMUTH B. ET AL: "Purification and properties of an NADPH-dependent carbonyl reductase from human brain. Relationship to prostaglandin 9-ketoreductase and xenobiotic ketone reductase", THE JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 256, no. 3, 10 February 1981 (1981-02-10), pages 1206 - 1213, XP002988257
PETERS J. ET AL: "A novel NADH-dependent carbonyl reductase with an extremely broad substrate range from Candida parapsilosis: purification and characterization", ENZYME AND MICROBIAL TECHNOLOGY, vol. 15, 1993, pages 950 - 958, XP001094911
See also references of EP 1715054A4
WHITNEY T.A. ET AL: "Asymmetric synthesis via lithium chelates", POLYMER REPRINTS, vol. 13, no. 2, 1972, pages 688 - 692, XP002988254
LETUNOVA A.B. ET AL: "Preparation of gama-acetopropyl alcohol from gama-butyrolactone", KHIMIKO-FARMATSEVTICHESKII ZHURNAL, vol. 11, no. 12, 1977, pages 121 - 123, XP002988255
KIM ET AL: "The efficient resolution of protected diols and hydroxy aldehydes by lipases : Steric auxiliary approach and aynthetic applications.", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 6, no. 1, 1996, pages 71 - 76, XP004135126
WERMUTH B. ET AL: "Purification and properties of an NADPH-dependent carbonyl reductase from human brain. Relationship to prostaglandin 9-ketoreductase and xenobiotic ketone reductase", THE JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 256, no. 3, 10 February 1981 (1981-02-10), pages 1206 - 1213, XP002988257
PETERS J. ET AL: "A novel NADH-dependent carbonyl reductase with an extremely broad substrate range from Candida parapsilosis: purification and characterization", ENZYME AND MICROBIAL TECHNOLOGY, vol. 15, 1993, pages 950 - 958, XP001094911
See also references of EP 1715054A4
Attorney, Agent or Firm:
KANEKA CORPORATION (Kita-ku Osaka-shi, Osaka 88, JP)
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