Heterocycles p. 719 - 726 (2015)
Update date:2022-08-28
Topics:
Ding, Ding
Pan, Xianhua
Yu, Wansheng
Li, Xiaojun
Chen, Suke
Liu, Feng
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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