3-Aminopyrrolidines from -Aminoacids: Total Synthesis of (+)-Nemonapride from D-Alanine

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• 作者：Cam Thuy Hoang ; Viet Hoang Nguyen ; Valé ; rie Alezra ; Cyrille Kouklovsky
• 刊名：Journal of Organic Chemistry
• 出版年：2008
• 出版时间：February 1, 2008
• 年：2008
• 卷：73
• 期：3
• 页码：1162 - 1164
• 全文大小：49K
• 年卷期：v.73,no.3(February 1, 2008)
• ISSN：1520-6904

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The antipsychotic compound nemonapride 1 was synthesizedin nine steps from D-alanine 2. The key steps for the synthesisof the 3-aminopyrrolidine moiety include a Birch reductionof a cyclic enaminoester and the reduction of a pyrrolidinoneto the pyrrolidine 7. Final coupling with the benzoic acidderivative 9 gave 1 as a single enantio- and diastereomer.