Optically active pyrrolidine derivative, production and use thereof

Abstract

Abstract NEW MATERIAL:A compound shown by formula I [X is amino-protecting group of -COR<1>(R<1> is t-butyloxy, phenyl, etc.) or H; Y is H, methyl, ethyl, acetyl, etc.; R<2> and R<3> are H or carboxyl-protecting group; Z is H, OH, alkoxy, etc.; the second and the fifth positions are in (S) and (R) configuration, respectively]. EXAMPLE:1-Benzyloxycarbonyl-2(S)-methoxycarbonyl-5-methoxypyrrolidine. USE:An intermediate for synthesizing carbapenem of beta-lactam antibiotics by a simple production process at low cost. PREPARATION:A pyrrolidine derivative shown by formula II is reacted with a carbon nucleophilic reagent (e.g. ketene silyl acetal, acetoacetic ester or malonic ester) in the presence of Lewis acid to give a compound shown by formula I.

Inventors

• 👤 Tatsuya Shono
• 👤 庄野　達哉
• 👤 Kunisuke Izawa
• 👤 井沢　邦輔
• 👤 Shoichi Asada
• 👤 浅田　昌一
• 👤 Seiichi Nishi
• 👤 誠一 西
• 👤 Koji Asai
• 👤 浅井　康二

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