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WO2013007371A3 - Kinetic resolution of chiral amines - Google Patents

Kinetic resolution of chiral amines Download PDF

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Publication number
WO2013007371A3
WO2013007371A3 PCT/EP2012/002884 EP2012002884W WO2013007371A3 WO 2013007371 A3 WO2013007371 A3 WO 2013007371A3 EP 2012002884 W EP2012002884 W EP 2012002884W WO 2013007371 A3 WO2013007371 A3 WO 2013007371A3
Authority
WO
WIPO (PCT)
Prior art keywords
kinetic resolution
chiral
chiral amines
amine
kinetic
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/EP2012/002884
Other languages
French (fr)
Other versions
WO2013007371A2 (en
Inventor
Jeffrey Bode
Michael BINANZER
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eidgenoessische Technische Hochschule Zurich ETHZ
Original Assignee
Eidgenoessische Technische Hochschule Zurich ETHZ
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 Eidgenoessische Technische Hochschule Zurich ETHZ filed Critical Eidgenoessische Technische Hochschule Zurich ETHZ
Publication of WO2013007371A2 publication Critical patent/WO2013007371A2/en
Publication of WO2013007371A3 publication Critical patent/WO2013007371A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
    • C07D211/60—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
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
    • C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/08—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
    • 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
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The present invention refers to a method for the kinetic resolution of a chiral primary or secondary amine by treating the amine with a chiral, hydroxamic acid derived reagent of the formula (I). These chiral reagents are particularly useful for the kinetic resolution of cyclic amines and may be generated in situ in the presence of an N-heterocyclic carbene, thus allowing for a catalytic reaction.
PCT/EP2012/002884 2011-07-13 2012-07-09 Kinetic resolution of chiral amines Ceased WO2013007371A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP11005706 2011-07-13
EP11005706.4 2011-07-13

Publications (2)

Publication Number Publication Date
WO2013007371A2 WO2013007371A2 (en) 2013-01-17
WO2013007371A3 true WO2013007371A3 (en) 2013-10-03

Family

ID=46514300

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2012/002884 Ceased WO2013007371A2 (en) 2011-07-13 2012-07-09 Kinetic resolution of chiral amines

Country Status (1)

Country Link
WO (1) WO2013007371A2 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3177616B1 (en) 2014-08-04 2021-02-24 Sandoz AG Novel routes of synthesis for the preparation of suvorexant
WO2019152527A1 (en) * 2018-01-30 2019-08-08 Board Of Regents, The University Of Texas System Pipecolic esters for inhibition of the proteasome
CN112279765B (en) * 2019-07-24 2022-06-10 中国科学院福建物质结构研究所 Preparation method of chiral alpha-fluoroketone compound
CN112299996B (en) * 2019-07-24 2022-06-10 中国科学院福建物质结构研究所 Synthesis method of chiral alpha-deuterated ketone

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0384594A1 (en) * 1989-02-03 1990-08-29 The Wellcome Foundation Limited Anti-inflammatory aryl derivatives
EP0564129A2 (en) * 1992-03-23 1993-10-06 University Of Notre Dame Process for the preparation of 3-substituted-2-azetidinones
WO2008115153A1 (en) * 2007-03-22 2008-09-25 Agency For Science, Technology And Research N-heterocyclic carbene (nhc) catalyzed synthesis of hydroxamic acids

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0384594A1 (en) * 1989-02-03 1990-08-29 The Wellcome Foundation Limited Anti-inflammatory aryl derivatives
EP0564129A2 (en) * 1992-03-23 1993-10-06 University Of Notre Dame Process for the preparation of 3-substituted-2-azetidinones
WO2008115153A1 (en) * 2007-03-22 2008-09-25 Agency For Science, Technology And Research N-heterocyclic carbene (nhc) catalyzed synthesis of hydroxamic acids

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
A.G. AL-SEHEMI ET AL, CHEMICAL COMMUNICATIONS, 2001, pages 2684 - 2685, XP002669431 *
D.J. BROOKS ET AL, JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 2: PHYSICAL ORGONIC CHEMISTRY, no. 3, 1992, pages 393 - 396, XP002669001 *
H.U. VORA ET AL, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 129, no. 45, 2007, pages 13796 - 13797, XP002669429 *
P.-C. CHIANG ET AL, CHEMICAL COMMUNICATIONS, 2009, pages 4566 - 4568, XP002669002 *
S. HANESSIAN ET AL, SYNLETT, no. 6, 1995, pages 633 - 634, XP002669000 *
S. IWAHANA ET AL, CHEMISTRY - A EUROPEAN JOURNAL, vol. 17, no. 29, 11 July 2011 (2011-07-11), pages 8009 - 8013, XP002669430 *
V.P. KRASNOV ET AL, TETRAHEDRON ASYMMETRY, vol. 15, no. 5, 8 March 2004 (2004-03-08), pages 859 - 862, XP004493049, ISSN: 0957-4166, DOI: 10.1016/J.TETASY.2004.01.025 *
Y. OKUMURA ET AL, TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 58, no. 43, 21 October 2002 (2002-10-21), pages 8729 - 8736, XP004390180, ISSN: 0040-4020, DOI: 10.1016/S0040-4020(02)01090-6 *

Also Published As

Publication number Publication date
WO2013007371A2 (en) 2013-01-17

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