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■ An Cost-Effective and Safe Process of L-cis-4,5-Methanoproline Amide, the Key Synthetic Intermediate of Saxagliptin, via an Improved Simmons-Smith Reaction
Ding ding, Xianhua Pan, Wansheng Yu, Xiaojun Li, Suke Chen, and Feng Liu*
*School of Perfume and Aroma Technology, Shanghai Institute of Technology, Haiquan Rd. 100 Shanghai, 201418, China
Abstract
L-cis-4,5-Methanoproline amide, a key intermediate of saxagliptin, was synthesized by an improved Simmons-Smith reaction. The zinc carbenoid was formed through Zn/CuBr and CH2I2, under the optimized condition, the title compound was gained with 68% yield and excellent diastereomeric selectivity (40:1 d.r.). The absence of the flammable and expensive ZnEt2 makes this procedure very attractive in large scale production.
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