PROCESS FOR PRODUCTION OF CYCLOPENTENENITRILE DERIVATIVES

Title:

PROCESS FOR PRODUCTION OF CYCLOPENTENENITRILE DERIVATIVES

Document Type and Number:

WIPO Patent Application WO/2005/085184

Kind Code:

A1

Abstract:

[PROBLEMS] To provide a process for the synthesis of cyclopentenenitrile derivatives through conjugate addition of a nitrile derivative to an &agr ,β-unsaturated ketone whereby cyclopentenenitrile derivatives, particularly those capable of optical resolution, can be obtained in high yield without expensive reagents or compounds in a decreased number of steps. [MEANS FOR SOLVING PROBLEMS] A novel process for the production of cyclopentenenitrile derivatives in high yield, which comprises trapping a compound obtained by conjugate addition of a 4-alkoxy-3-butenenitrile which may have alkyl or allyl at the &agr -position (e.g., 4-methoxy-3-butenenitrile) to an &agr ,β- unsaturated ketone as an enol ester with acetic anhydride, chlorocarbonic ester, or the like and treating the enol ester with a strong acid or the like to form a five-membered ring.

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Inventors:

MIYASHITA MASAAKI (JP)
TANINO KEIJI (JP)
TOMATA YOSHIHIDE (JP)
SHIINA YASUHIRO (JP)

Application Number:

PCT/JP2005/003900

Publication Date:

September 15, 2005

Filing Date:

March 07, 2005

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Assignee:

JAPAN SCIENCE & TECH AGENCY (JP)
MIYASHITA MASAAKI (JP)
TANINO KEIJI (JP)
TOMATA YOSHIHIDE (JP)
SHIINA YASUHIRO (JP)

International Classes:

C07B53/00; C07B57/00; C07C253/30; C07C255/47; C12P13/00; C12P41/00; (IPC1-7): C07C253/30; C07B53/00; C07B57/00; C07C255/47; C12P41/00

Foreign References:

JP2003286266A	2003-10-10
JPS4942660A	1974-04-22

Other References:

MATSUOKA H. ET AL: "Easy preparation method for 2-thioxopyrrolidine derovatives including 3-hydroxymethylene-2-thioxopyrrolidine, an antimicrobial degradation product of radish pungent principle, via (E,Z)-4-methoxy-3-butenyl isothiocyanate.", BIOSCIENCE, BIOTECHNOLOGY, AND BIOCHEMISTRY., vol. 60, no. 5, 1996, pages 914 - 915, XP002990313
KATSNEL'SON M.G. ET AL: "Dealkoxylation of dymethyl acetal of beta-cyanopropionaldehyde.", ZHURNAL PRIKLADNOI KHIMII., vol. 54, no. 3, 1981, pages 648 - 651, XP002990314

Attorney, Agent or Firm:

Saeki, Norio (Aminosan Kaikan Building 15-8, Nihonbashi 3-chom, Chuo-ku Tokyo 27, JP)

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