Organic Process Research and Development p. 1784 - 1795 (2015)
Update date:2022-08-03
Topics:
Zhang, Wu-Yan
Hogan, Philip C.
Chen, Chi-Li
Niu, John
Wang, Zhimin
Lafrance, Danny
Gilicky, Olga
Dunwoody, Nicholas
Ronn, Magnus
A robust, cost-effective, and high yielding manufacturing process for enantiomerically enriched (S)-allylic amine 3, a key intermediate for fully synthetic tetracyclines have been developed. Two novel and scalable asymmetric vinylations resulting in high-to-excellent stereoselectivity have been developed for the key step. The final product is purified by an efficient crystallization of a l-tartaric salt. The process described has been used to manufacture ~350 kg of the tartaric salt of 3 with 99.0% ee in 8 steps (35% overall yield) from cheap and readily available dimethyl maleate.
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