Method of preparing cyclopentene nitrile derivatives

• Main Authors: TANINO, KEIJI, MIYASHITA, MASAAKI, TOMATA, YOSHIHIDE, SHIINA, YASUHIRO
• Format: Patent
• Language: Chinese; English
• Published: 01.02.2006
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; APPARATUS THEREFOR; BEER; BIOCHEMISTRY; CHEMISTRY; ENZYMOLOGY; FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIREDCHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERSFROM A RACEMIC MIXTURE; GENERAL METHODS OF ORGANIC CHEMISTRY; METALLURGY; MICROBIOLOGY; MUTATION OR GENETIC ENGINEERING; ORGANIC CHEMISTRY; SPIRITS; VINEGAR; WINE

The present invention is aimed to provide a method of preparing cyclopentene nitrile derivatives, especially optically resolvable cyclopentene nitrile derivatives, by subjecting a nitrile derivative and an , -unsaturated ketone to conjugate addition reaction. The method has the advantages such as good yield, fewer steps, and no need of using expensive reagents or compounds. More specifically, the present invention is related to a novel method of preparing cyclopentene nitrile derivatives in good yield, comprising subjecting an 4-alkoxy-3-butenonitrile derivative (for example, 4-methoxy-3-butenonitrile) which may optionally have an alkyl or ally group on the -position and an , -unsaturated ketone to conjugate addition reaction, then treating the resulting product with acetic anhydride or chlorocarbonate to form an enol ester, and finally treating the enol ester with a strong acid to form a 5-membered ring, thereby forming the cyclopentene nitrile derivative.