An Efficient and Scalable Synthesis of tert-Butyl (3aR,6aS)-5-Oxohexahydrocyclo penta[c]pyrrole-2(1H)-carboxylate: A Pharmacologically Important Intermediate

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• 作者：Rajesh H. BahekarPradip A. Jadav ; Amitgiri D. Goswami ; Hardik A. Shah ; Bhushan N. Dave ; Darshan A. Joshi ; Jignesh P. Pethani ; Dipam Patel ; Sameer Agarwal ; Ranjit C. Desai
• 刊名：Organic Process Research & Development
• 出版年：2017
• 出版时间：February 17, 2017
• 年：2017
• 卷：21
• 期：2
• 页码：266-272
• 全文大小：365K
• ISSN：1520-586X

文摘

Hexahydrocyclopentapyrrolone derivatives constitute an important class of bicycles, and it represents an essential pharmacophore for diversified pharmacological activities. A highly efficient process for the synthesis of tert-butyl(3aR,6aS)-5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate 1 has been developed. The improved process involves transformation of isoindole 4 to diacid 5, using an inexpensive KMnO₄ mediated oxidative cleavage as a key step. The developed process was cost-effective, high yielding, kilogram scalable, and commercially viable for synthesis of 1.