CA2134096C - Enantioselective oxazaborolidine catalysts - Google Patents

Enantioselective oxazaborolidine catalysts

Info

Publication number
CA2134096C
CA2134096C CA002134096A CA2134096A CA2134096C CA 2134096 C CA2134096 C CA 2134096C CA 002134096 A CA002134096 A CA 002134096A CA 2134096 A CA2134096 A CA 2134096A CA 2134096 C CA2134096 C CA 2134096C
Authority
CA
Canada
Prior art keywords
phenyl
alkyl
carbon atom
chiral
configuration
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.)
Expired - Fee Related
Application number
CA002134096A
Other languages
English (en)
French (fr)
Other versions
CA2134096A1 (en
Inventor
George J. Quallich
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.)
Pfizer Ltd
Original Assignee
Pfizer Ltd
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 Pfizer Ltd filed Critical Pfizer Ltd
Publication of CA2134096A1 publication Critical patent/CA2134096A1/en
Application granted granted Critical
Publication of CA2134096C publication Critical patent/CA2134096C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/24—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/025—Boronic and borinic acid compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated

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)
  • Physical Or Chemical Processes And Apparatus (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Catalysts (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Polyurethanes Or Polyureas (AREA)
CA002134096A 1992-05-14 1993-02-01 Enantioselective oxazaborolidine catalysts Expired - Fee Related CA2134096C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US88331792A 1992-05-14 1992-05-14
US883,317 1992-05-14

Publications (2)

Publication Number Publication Date
CA2134096A1 CA2134096A1 (en) 1993-11-25
CA2134096C true CA2134096C (en) 1997-11-25

Family

ID=25382382

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002134096A Expired - Fee Related CA2134096C (en) 1992-05-14 1993-02-01 Enantioselective oxazaborolidine catalysts

Country Status (21)

Country Link
US (1) US5552548A (cg-RX-API-DMAC7.html)
EP (1) EP0640089B1 (cg-RX-API-DMAC7.html)
JP (1) JP2525127B2 (cg-RX-API-DMAC7.html)
KR (2) KR950701637A (cg-RX-API-DMAC7.html)
AT (1) ATE146790T1 (cg-RX-API-DMAC7.html)
AU (1) AU659929B2 (cg-RX-API-DMAC7.html)
CA (1) CA2134096C (cg-RX-API-DMAC7.html)
DE (1) DE69306945T2 (cg-RX-API-DMAC7.html)
DK (1) DK0640089T3 (cg-RX-API-DMAC7.html)
ES (1) ES2096275T3 (cg-RX-API-DMAC7.html)
FI (1) FI107259B (cg-RX-API-DMAC7.html)
GR (1) GR3022171T3 (cg-RX-API-DMAC7.html)
HU (1) HU215089B (cg-RX-API-DMAC7.html)
IL (1) IL105623A (cg-RX-API-DMAC7.html)
MX (1) MX9302785A (cg-RX-API-DMAC7.html)
MY (1) MY111251A (cg-RX-API-DMAC7.html)
NO (1) NO300500B1 (cg-RX-API-DMAC7.html)
NZ (1) NZ249302A (cg-RX-API-DMAC7.html)
TW (1) TW232696B (cg-RX-API-DMAC7.html)
WO (1) WO1993023408A1 (cg-RX-API-DMAC7.html)
ZA (1) ZA933340B (cg-RX-API-DMAC7.html)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06329679A (ja) * 1993-01-20 1994-11-29 Nissan Chem Ind Ltd 光学活性β−アミノアルコキシボラン錯体
TW416958B (en) * 1993-05-14 2001-01-01 Pfizer Enantioselective oxazaborolidine catalysts
CA2167287A1 (en) * 1993-07-16 1995-01-26 George Joseph Quallich Enantioselective process for thiazole intermediates
EP0724552B1 (en) * 1993-11-30 1997-10-29 Pfizer Inc. Process for preparing a chiral tetralone
US5495054A (en) * 1994-05-31 1996-02-27 Sepracor, Inc. Tetrahydroindeno[1,2-D][1,3,2]oxazaboroles and their use as enantioselective catalysts
AU2792497A (en) * 1996-09-18 1998-04-14 Shionogi & Co., Ltd. Process for preparing optically acitve alcohol by reduction with asymmetric borane
ES2130083B1 (es) * 1997-08-04 2000-01-16 Esteve Labor Dr Procedimiento para la obtencion de los enantiomeros de cizolirtina.
US6509472B2 (en) * 2000-09-11 2003-01-21 Schering Corporation 4-Cyclohexyl-1,3,2-oxazaborolidine chiral accessories
DK2035437T3 (da) * 2006-06-26 2010-11-29 Basf Se Boran-æter-komplekser
US20080242877A1 (en) * 2007-02-26 2008-10-02 Vinod Kumar Kansal Intermediates and processes for the synthesis of Ramelteon
US7838691B2 (en) * 2007-04-05 2010-11-23 Board Of Regents, Of The University Of Texas System Palmerolides: methods of preparation and derivatives thereof
JP2010526075A (ja) * 2007-04-30 2010-07-29 アドロー コーポレイション （−）−ｅ−１０−ｏｈ−ｎｔの組成物、ならびにそれらの合成および使用のための方法
US8084630B2 (en) * 2007-05-31 2011-12-27 Teva Pharmaceutical Industries Ltd. Process for the synthesis of ramelteon and its intermediates
US20090082568A1 (en) * 2007-09-21 2009-03-26 Basf Aktiengesellschaft Accelerated reduction of organic substances with boranes
US20090281176A1 (en) * 2007-11-01 2009-11-12 Vinod Kumar Kansal Process for the synthesis of ramelteon and its intermediates
US20100152468A1 (en) * 2008-10-16 2010-06-17 Teva Pharmaceutical Industries Ltd. Process for the synthesis of ramelteon and its intermediates

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4943635A (en) * 1987-08-27 1990-07-24 President & Fellows Of Harvard College Enantioselective reduction of ketones
US5157129A (en) * 1990-04-18 1992-10-20 Merck & Co., Inc. Enantiospecific synthesis of s-(+)-5,6-dihydro-4-(r-amino)-4h-thieno(2,3-b)thiopyran-2-sulfonamide-7,7-dioxide
US5039802A (en) * 1990-04-18 1991-08-13 Merck & Co., Inc. Arylation process for preparation of chiral catalysts for ketone reduction
JPH06329679A (ja) * 1993-01-20 1994-11-29 Nissan Chem Ind Ltd 光学活性β−アミノアルコキシボラン錯体
TW416958B (en) * 1993-05-14 2001-01-01 Pfizer Enantioselective oxazaborolidine catalysts

Also Published As

Publication number Publication date
EP0640089A1 (en) 1995-03-01
KR0149208B1 (ko) 1998-10-15
FI932174L (fi) 1993-11-15
KR950701637A (ko) 1995-04-28
ZA933340B (en) 1994-11-14
MX9302785A (es) 1994-02-28
JPH07503734A (ja) 1995-04-20
GR3022171T3 (en) 1997-03-31
US5552548A (en) 1996-09-03
JP2525127B2 (ja) 1996-08-14
AU3593193A (en) 1993-12-13
FI107259B (fi) 2001-06-29
EP0640089B1 (en) 1996-12-27
HUT65136A (en) 1994-04-28
DK0640089T3 (da) 1997-06-16
ES2096275T3 (es) 1997-03-01
FI932174A0 (fi) 1993-05-13
TW232696B (cg-RX-API-DMAC7.html) 1994-10-21
MY111251A (en) 1999-10-30
NZ249302A (en) 1996-11-26
AU659929B2 (en) 1995-06-01
HU215089B (hu) 1998-09-28
DE69306945D1 (de) 1997-02-06
CA2134096A1 (en) 1993-11-25
ATE146790T1 (de) 1997-01-15
NO944297D0 (no) 1994-11-11
IL105623A (en) 1998-02-22
WO1993023408A1 (en) 1993-11-25
DE69306945T2 (de) 1997-05-07
IL105623A0 (en) 1993-09-22
HU9301395D0 (en) 1993-09-28
NO300500B1 (no) 1997-06-09
NO944297L (no) 1994-11-11

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