WO2008090819A1 - 二環性プロリン化合物の製造方法 - Google Patents

二環性プロリン化合物の製造方法 Download PDF

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Publication number
WO2008090819A1
WO2008090819A1 PCT/JP2008/050607 JP2008050607W WO2008090819A1 WO 2008090819 A1 WO2008090819 A1 WO 2008090819A1 JP 2008050607 W JP2008050607 W JP 2008050607W WO 2008090819 A1 WO2008090819 A1 WO 2008090819A1
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WO
WIPO (PCT)
Prior art keywords
formula
compound represented
compound
hydrogen atom
production
Prior art date
Application number
PCT/JP2008/050607
Other languages
English (en)
French (fr)
Inventor
Takayuki Hamada
Original Assignee
Ajinomoto Co., Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ajinomoto Co., Inc. filed Critical Ajinomoto Co., Inc.
Publication of WO2008090819A1 publication Critical patent/WO2008090819A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyrrole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Indole Compounds (AREA)

Abstract

　工業的製造に適した光学活性３－アザビシクロ［３．３．０］オクタン－２－カルボン酸に代表される二環性プロリン化合物の製造方法の提供。 　式（１）で表される化合物を、塩基存在下、式（２）で表されるシクロペンテン－１－カルボアルデヒドと反応させ、式（３）で表される化合物を得る。式（３）で表される化合物を酸で処理し、式（４）で表される化合物を得る。式（４）で表される化合物を得た後、さらに還元反応を行う工程、及びアミノ基を保護基で保護するか又は保護しない工程を経て、式（５）で表される二環性プロリン化合物又はその塩に誘導する。 ［式中、Ｘは水素原子又は塩素原子を示し、＊１、＊２、＊３及び＊４は不斉炭素原子であることを示し、不斉炭素原子の立体配置はＳ又はＲである。＊１、＊２、＊３及び＊４の不斉炭素原子の立体配置はそれぞれＳ，Ｓ，Ｓ，Ｒ又はＲ，Ｒ，Ｒ，Ｓである。Ｒ１及びＲ２は、それぞれ独立に水素原子又はカルボキシル基の保護基を示す。Ｐは水素原子又はアミノ基の保護基を示す。］
PCT/JP2008/050607 2007-01-23 2008-01-18 二環性プロリン化合物の製造方法 WO2008090819A1 (ja)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2007012361A JP2010090031A (ja) 2007-01-23 2007-01-23 二環性プロリン化合物の製造方法
JP2007-012361 2007-01-23

Publications (1)

Publication Number Publication Date
WO2008090819A1 true WO2008090819A1 (ja) 2008-07-31

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2008/050607 WO2008090819A1 (ja) 2007-01-23 2008-01-18 二環性プロリン化合物の製造方法

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JP (1) JP2010090031A (ja)
WO (1) WO2008090819A1 (ja)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014033667A1 (en) 2012-08-30 2014-03-06 Ranbaxy Laboratories Limited Process for the preparation of telaprevir
WO2014096374A1 (en) 2012-12-21 2014-06-26 Sandoz Ag Process for the synthesis of pyrrolidines and pyrroles
WO2014203208A1 (en) 2013-06-21 2014-12-24 Ranbaxy Laboratories Limited Process for the preparation of telaprevir and intermediates thereof
WO2014203224A1 (en) 2013-06-21 2014-12-24 Ranbaxy Laboratories Limited Process for the preparation of telaprevir and its intermediates

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5829529B2 (ja) * 2011-08-29 2015-12-09 日本曹達株式会社 光学活性４級アンモニウム塩、および光学活性化合物の製造方法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BERGMEIER S.C. ET AL.: "Synthesis of bicyclic proline analogs using a formal [3 + 2] intramolecular aziridine-allylsilane cycloaddition reaction", TETRAHEDRON, vol. 55, no. 26, 1999, pages 8025 - 8038, XP004168571, DOI: doi:10.1016/S0040-4020(99)00425-1 *
MONN J.A. ET AL.: "A Concise, Stereocontrolled Thiazolium Ylide Approach to Kainic Acid", JOURNAL OF ORGANIC CHEMISTRY, vol. 59, no. 10, 1994, pages 2773 - 2778, XP002419726, DOI: doi:10.1021/jo00089a022 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014033667A1 (en) 2012-08-30 2014-03-06 Ranbaxy Laboratories Limited Process for the preparation of telaprevir
WO2014096374A1 (en) 2012-12-21 2014-06-26 Sandoz Ag Process for the synthesis of pyrrolidines and pyrroles
WO2014203208A1 (en) 2013-06-21 2014-12-24 Ranbaxy Laboratories Limited Process for the preparation of telaprevir and intermediates thereof
WO2014203224A1 (en) 2013-06-21 2014-12-24 Ranbaxy Laboratories Limited Process for the preparation of telaprevir and its intermediates

Also Published As

Publication number Publication date
JP2010090031A (ja) 2010-04-22

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