Practical Large-Scale Synthesis of 3,4-Isopropylidenedioxypyrrolidine Hydrotosylate: Atom Economical Self-Hydrogenolysis of a Crystalline Borane-Benzylamine Adduct

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• 作者：Michel Couturier ; Brian M. Andresen ; Jeffrey B. Jorgensen ; John L. Tucker ; Frank R. Busch ; Steven J. Brenek ; Pascal Dubé ; David J. am Ende ; and Joanna T. Negri
• 刊名：Organic Process Research & Development
• 出版年：2002
• 出版时间：January 2002
• 年：2002
• 卷：6
• 期：1
• 页码：42 - 48
• 全文大小：101K
• 年卷期：v.6,no.1(January 2002)
• ISSN：1520-586X

文摘

An efficient four-step sequence has been developed for thesynthesis of 3,4-isopropylidenedioxypyrrolidine hydrotosylatestarting from inexpensive N-benzylmaleimide. This approachfeatures a novel N-debenzylation procedure that utilizes thecorresponding borane-benzylamine complex as an internalhydrogen-transfer source. This palladium-catalyzed tandemprotonolysis/hydrogenolysis allows cleavage of the borane-amine adduct and debenzylation in a single operation.