WO2009044803A1 - 不斉触媒マイケル反応生成物の製造方法 - Google Patents

不斉触媒マイケル反応生成物の製造方法 Download PDF

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Publication number
WO2009044803A1
WO2009044803A1 PCT/JP2008/067923 JP2008067923W WO2009044803A1 WO 2009044803 A1 WO2009044803 A1 WO 2009044803A1 JP 2008067923 W JP2008067923 W JP 2008067923W WO 2009044803 A1 WO2009044803 A1 WO 2009044803A1
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WIPO (PCT)
Prior art keywords
asymmetric
catalyst
michael reaction
producing product
nitroalkane
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PCT/JP2008/067923
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English (en)
French (fr)
Inventor
Yujiro Hayashi
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Tokyo University Of Science Educational Foundation Administrative Organization
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Publication of WO2009044803A1 publication Critical patent/WO2009044803A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/44—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by —CHO groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B53/00—Asymmetric syntheses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/04—Formation of amino groups in compounds containing carboxyl groups
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

　α，β－不飽和アルデヒドとニトロメタン等のニトロアルカンとから、対応するマイケル付加体を高い不斉収率で得ることが可能な不斉触媒マイケル反応生成物の製造方法を提供する。 　α，β－不飽和アルデヒドとニトロアルカンとの不斉触媒マイケル反応において、下記一般式（３）で表される不斉触媒又はそのエナンチオマーを用いる。 ［式中、Ｒ４，Ｒ５は、それぞれ独立に置換基を有していてもよいアリール基、ヘテロアリール基、シクロアルキル基、ヘテロシクロアルキル基、シクロアルケニル基、ヘテロシクロアルケニル基、アルキル基、アルケニル基、又はアルキニル基を示し、Ｒ６は、水素原子、シリル基、又はアルキル基を示し、Ｒ７は、水酸基の保護基を示し、ｎは０又は１を示す。］
PCT/JP2008/067923 2007-10-04 2008-10-02 不斉触媒マイケル反応生成物の製造方法 WO2009044803A1 (ja)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2007-260468 2007-10-04
JP2007260468A JP5234901B2 (ja) 2007-10-04 2007-10-04 不斉触媒マイケル反応生成物の製造方法

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WO2009044803A1 true WO2009044803A1 (ja) 2009-04-09

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JP (1) JP5234901B2 (ja)
WO (1) WO2009044803A1 (ja)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009141362A2 (en) * 2008-05-21 2009-11-26 Sandoz Ag Process for the stereoselective enzymatic hydrolysis of 5-methyl-3-nitromethyl-hexanoic acid ester
CN103304599A (zh) * 2013-06-20 2013-09-18 中国科学院福建物质结构研究所 二苯基乙二胺衍生的磷酰胺手性化合物及其制备和应用
CN103547558A (zh) * 2011-04-28 2014-01-29 小野药品工业株式会社 制备含五元环化合物的方法
CN104788370A (zh) * 2015-04-30 2015-07-22 中国科学技术大学 一种构型可控地合成2-(4-硝基)丁酰基吡啶氮-氧化合物的方法
WO2017009753A1 (en) 2015-07-13 2017-01-19 Piramal Enterprises Limited An improved process for the preparation of baclofen and its intermediate
CN108218649A (zh) * 2017-12-29 2018-06-29 联化科技股份有限公司 普瑞巴林及其中间体的合成方法
KR20190103933A (ko) 2018-02-28 2019-09-05 고려대학교 산학협력단 입체 선택성이 우수한 이 작용성 유기 키랄 촉매 화합물, 이의 제조 방법 및 이를 이용한 나이트로 화합물로부터의 비천연 감마-아미노산의 제조 방법

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3154930B1 (en) * 2014-06-12 2018-04-18 Siegfried Ltd. Method for the preparation of beta-substituted gamma-amino carboxylic acids

Citations (2)

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Publication number Priority date Publication date Assignee Title
JPH11506098A (ja) * 1995-06-02 1999-06-02 ワーナー−ランバート・コンパニー （ｓ）−３−（アミノメチル）−５−メチルヘキサン酸を製造する方法
JP2006151839A (ja) * 2004-11-26 2006-06-15 Univ Of Tokyo α，β−不飽和カルボン酸誘導体からのエナンチオ選択的β−シアノカルボン酸誘導体の調製方法、及び該方法に用いる触媒

Family Cites Families (1)

* Cited by examiner, † Cited by third party
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CN101300224A (zh) * 2005-04-11 2008-11-05 特瓦制药工业有限公司 制备(s)-普瑞巴林的方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11506098A (ja) * 1995-06-02 1999-06-02 ワーナー−ランバート・コンパニー （ｓ）−３−（アミノメチル）−５−メチルヘキサン酸を製造する方法
JP2006151839A (ja) * 2004-11-26 2006-06-15 Univ Of Tokyo α，β−不飽和カルボン酸誘導体からのエナンチオ選択的β−シアノカルボン酸誘導体の調製方法、及び該方法に用いる触媒

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Title
BURK J. MARK ET AL., JOURNAL OF ORGANIC CHEMISTRY, vol. 68, 2003, pages 5731 - 5734 *
COREY E.J. ET AL., ORGANIC LETTERS, vol. 2, 2000, pages 4257 - 4259 *
GOTOH HIROAKI ET AL., ORGANIC LETTERS, vol. 9, pages 5307 - 5309 *
OKINO TOMOTAKA ET AL., JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 127, 2005, pages 119 - 125 *
YUJIRO HAYASHI ET AL.: "86th Annual Meeting on Chemical Society of Japan in Spring-Koen Yokoshu II", 13 March 2006, pages: 1069 *

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009141362A3 (en) * 2008-05-21 2010-04-15 Sandoz Ag Process for the stereoselective enzymatic hydrolysis of 5-methyl-3-nitromethyl-hexanoic acid ester
US8546112B2 (en) 2008-05-21 2013-10-01 Sandoz Ag Process for the stereoselective enzymatic hydrolysis of 5-methyl-3-nitromethyl-hexanoic acid ester
EA019285B1 (ru) * 2008-05-21 2014-02-28 Сандоз Аг Способ стереоселективного ферментативного гидролиза эфира 5-метил-3-нитрометилгексановой кислоты
WO2009141362A2 (en) * 2008-05-21 2009-11-26 Sandoz Ag Process for the stereoselective enzymatic hydrolysis of 5-methyl-3-nitromethyl-hexanoic acid ester
CN103547558B (zh) * 2011-04-28 2016-03-16 小野药品工业株式会社 制备含五元环化合物的方法
CN103547558A (zh) * 2011-04-28 2014-01-29 小野药品工业株式会社 制备含五元环化合物的方法
CN103304599A (zh) * 2013-06-20 2013-09-18 中国科学院福建物质结构研究所 二苯基乙二胺衍生的磷酰胺手性化合物及其制备和应用
CN104788370A (zh) * 2015-04-30 2015-07-22 中国科学技术大学 一种构型可控地合成2-(4-硝基)丁酰基吡啶氮-氧化合物的方法
WO2017009753A1 (en) 2015-07-13 2017-01-19 Piramal Enterprises Limited An improved process for the preparation of baclofen and its intermediate
CN108218649A (zh) * 2017-12-29 2018-06-29 联化科技股份有限公司 普瑞巴林及其中间体的合成方法
CN108218649B (zh) * 2017-12-29 2021-07-30 联化科技股份有限公司 普瑞巴林及其中间体的合成方法
KR20190103933A (ko) 2018-02-28 2019-09-05 고려대학교 산학협력단 입체 선택성이 우수한 이 작용성 유기 키랄 촉매 화합물, 이의 제조 방법 및 이를 이용한 나이트로 화합물로부터의 비천연 감마-아미노산의 제조 방법
KR20200117952A (ko) 2018-02-28 2020-10-14 고려대학교 산학협력단 입체 선택성이 우수한 이 작용성 유기 키랄 촉매 화합물, 이의 제조 방법 및 이를 이용한 나이트로 화합물로부터의 비천연 감마-아미노산의 제조 방법

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JP5234901B2 (ja) 2013-07-10
JP2009091257A (ja) 2009-04-30

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