Asymmetric synthesis and pharmacology of methylphenidate and its para-substituted derivatives

DL Thai, MT Sapko, CT Reiter, DE Bierer…

文献索引：Thai, Dung L.; Sapko, Michael T.; Reiter, Clara T.; Bierer, Donald E.; Perel, James M. Journal of Medicinal Chemistry, 1998 , vol. 41, # 4 p. 591 - 601

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被引用次数: 54

摘要

We report the first asymmetric synthesis of the individual enantiomers of methylphenidate (1). From d-pipecolic acid, the (2 R, 2'R) and (2 S, 2'R) enantiomers of 1 were obtained in> 99% optical purity while the (2 S, 2'S) and (2 R, 2'S) enantiomers of 1 were derived from l- pipecolic acid in 96% optical purity. The versatility of this methodology is demonstrated with the synthesis of the (2 R, 2'R) and (2 S, 2'S) enantiomers of p-bromo and p-methoxy ...