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WO2007010387A3 - Stereoselective synthesis of 3,4-disubstituted cyclopentanones and related compounds - Google Patents

Stereoselective synthesis of 3,4-disubstituted cyclopentanones and related compounds Download PDF

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Publication number
WO2007010387A3
WO2007010387A3 PCT/IB2006/002060 IB2006002060W WO2007010387A3 WO 2007010387 A3 WO2007010387 A3 WO 2007010387A3 IB 2006002060 W IB2006002060 W IB 2006002060W WO 2007010387 A3 WO2007010387 A3 WO 2007010387A3
Authority
WO
WIPO (PCT)
Prior art keywords
related compounds
stereoselective synthesis
cyclopentanones
disubstituted
disubstituted cyclopentanones
Prior art date
Application number
PCT/IB2006/002060
Other languages
French (fr)
Other versions
WO2007010387B1 (en
WO2007010387A2 (en
Inventor
Hans-Juergen Betche
Erwin Ayandra Irdam
Amphlett Greg Padilla
Bruce Pearlman
William Roland Perrault
John Vanalsten
Thaddeus S Franczyk
Original Assignee
Pharmacia & Upjohn Co Llc
Hans-Juergen Betche
Erwin Ayandra Irdam
Amphlett Greg Padilla
Bruce Pearlman
William Roland Perrault
John Vanalsten
Thaddeus S Franczyk
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 Pharmacia & Upjohn Co Llc, Hans-Juergen Betche, Erwin Ayandra Irdam, Amphlett Greg Padilla, Bruce Pearlman, William Roland Perrault, John Vanalsten, Thaddeus S Franczyk filed Critical Pharmacia & Upjohn Co Llc
Priority to CA002615490A priority Critical patent/CA2615490A1/en
Priority to EP06779907A priority patent/EP1912936A2/en
Publication of WO2007010387A2 publication Critical patent/WO2007010387A2/en
Publication of WO2007010387A3 publication Critical patent/WO2007010387A3/en
Publication of WO2007010387B1 publication Critical patent/WO2007010387B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/518—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of sulfur-containing compounds to >C = O groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/25—Sulfonic acids having sulfo groups bound to carbon atoms of rings other than six-membered aromatic rings of a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
    • C07C321/22—Thiols, sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/64—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton
    • C07C323/65—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfone or sulfoxide groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)
  • Indole Compounds (AREA)

Abstract

Methods and materials for preparing optically active 3,4-disubstituted cyclopentanones are disclosed. The method includes hydrolyzing one or more compounds represented by Formula (13), or removing an ester moiety from a compound represented by Formula (18).
PCT/IB2006/002060 2005-07-18 2006-07-13 Stereoselective synthesis of 3,4-disubstituted cyclopentanones and related compounds WO2007010387A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CA002615490A CA2615490A1 (en) 2005-07-18 2006-07-13 Stereoselective synthesis of 3,4-disubstituted cyclopentanones and related compounds
EP06779907A EP1912936A2 (en) 2005-07-18 2006-07-13 Stereoselective synthesis of 3,4-disubstituted cyclopentanones and related compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US70023505P 2005-07-18 2005-07-18
US60/700,235 2005-07-18

Publications (3)

Publication Number Publication Date
WO2007010387A2 WO2007010387A2 (en) 2007-01-25
WO2007010387A3 true WO2007010387A3 (en) 2007-04-26
WO2007010387B1 WO2007010387B1 (en) 2007-07-12

Family

ID=37487704

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2006/002060 WO2007010387A2 (en) 2005-07-18 2006-07-13 Stereoselective synthesis of 3,4-disubstituted cyclopentanones and related compounds

Country Status (6)

Country Link
EP (1) EP1912936A2 (en)
JP (1) JP2007023040A (en)
AR (1) AR057465A1 (en)
CA (1) CA2615490A1 (en)
TW (1) TW200745012A (en)
WO (1) WO2007010387A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5858581B2 (en) * 2012-09-27 2016-02-10 国立大学法人 東京大学 Method for producing indole 3-carboxylic acids
CN119306580A (en) * 2024-12-18 2025-01-14 大连来克精化有限公司 A preparation method of 3,4-dimethyl-1,2-cyclopentanedione

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002000584A1 (en) * 2000-06-28 2002-01-03 Warner-Lambert Company Cyclic ketones, their preparation and their use in the synthesis of amino acids
US6635673B1 (en) * 1997-10-27 2003-10-21 Warner-Lambert Company Cyclic amino acids and derivatives thereof useful as pharmaceutical agents

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6635673B1 (en) * 1997-10-27 2003-10-21 Warner-Lambert Company Cyclic amino acids and derivatives thereof useful as pharmaceutical agents
WO2002000584A1 (en) * 2000-06-28 2002-01-03 Warner-Lambert Company Cyclic ketones, their preparation and their use in the synthesis of amino acids

Non-Patent Citations (17)

* Cited by examiner, † Cited by third party
Title
C.M. PASSAROTTI ET AL., BOLL.CHIM.FARM., vol. 134, no. 9, 1995, pages 518 - 521 *
D. F. TABER ETAL.: "Diastereoselection in rhodium-mediated intramolecular C-H insertion: preparation of a trans-3,4-dialkyl cyclopentane", TETRAHEDRON LETTERS, vol. 26, no. 26, 1985, pages 3059 - 3062, XP002418684 *
DATABASE XFIRE Beilstein Institut zur Förderung der Chemischen Wissenschaften; XP002411091, Database accession no. 4444049 *
DATABASE XFIRE Beilstein Institut zur Förderung der Chemischen Wissenschaften; XP002411092, Database accession no. 10088938 *
DATABASE XFIRE Beilstein Institut zur Förderung der Chemischen Wissenschaften; XP002411093, Database accession no. 5741745 *
DATABASE XFIRE Beilstein Institut zur Förderung der Chemischen Wissenschaften; XP002411094, Database accession no. 7017701 *
DATABASE XFIRE Beilstein Institut zur Förderung der Chemischen Wissenschaften; XP002411095, Database accession no. 9626698 *
DATABASE XFIRE Beilstein Institut zur Förderung der Chemischen Wissenschaften; XP002411096, Database accession no. 3119741 *
K. KOJIMA ET AL.: "Stereospecific synthesis of functionalized cyclopentane derivatives", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 33, no. 7, 1985, pages 2750 - 2761, XP001249125 *
KOKKE W C M C ET AL: "TWO SYNTHESES OF OPTICALLY PURE (1R,2R)-1,2-DIMETHYLCYCLOPENTANE", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 39, no. 11, 5 April 1974 (1974-04-05), pages 1535 - 1539, XP001029096, ISSN: 0022-3263 *
N. KISE ET AL., J.ORG.CHEM., vol. 63, no. 22, 1998, pages 7931 - 7938 *
N. KISE ET AL.: "Stereoselective hydrocoupling of cinnamic acid esters by electroreduction: application to asymmetric synthesis of hydrodimers", JOURNAL OF ORGANIC CHEMISTRY, vol. 67, 2002, pages 8305 - 8315, XP002418685 *
P. MUELLER ET AL., HELV.CHIM.ACTA, vol. 77, no. 7, 1994, pages 1826 - 1836 *
U. AZZENA ET AL., TETRAHEDRON, vol. 61, no. 36, 2005, pages 8863 - 8668 *
U.M. DZHEMILEV ET AL., TETRAHEDRON, vol. 60, no. 6, 2004, pages 1281 - 1286 *
X.-F. ZHU ET AL.: "Stereospecific synthesis of carbonucleotides designed for antisense methodology", HELV.CHIM.ACTA, vol. 87, no. 9, 2004, pages 2245 - 2265, XP002411106 *
Y. SAKITO ET AL., CHEM. LETT., 1986, pages 621 - 624 *

Also Published As

Publication number Publication date
EP1912936A2 (en) 2008-04-23
TW200745012A (en) 2007-12-16
WO2007010387B1 (en) 2007-07-12
AR057465A1 (en) 2007-12-05
WO2007010387A2 (en) 2007-01-25
CA2615490A1 (en) 2007-01-25
JP2007023040A (en) 2007-02-01

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