Asymmetric synthesis and pharmacology of methylphenidate and its para-substituted derivatives
DL Thai, MT Sapko, CT Reiter, DE Bierer…
Index: 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
Full Text: HTML
Citation Number: 54
Abstract
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 ...
Related Articles:
Straightforward entry to the pipecolic acid nucleus. Enantioselective synthesis of baikiain
[Ginesta, Xavier; Pericas, Miquel A; Riera, Antoni Tetrahedron Letters, 2002 , vol. 43, # 5 p. 779 - 782]
[Beng, Timothy K.; Gawley, Robert E. Journal of the American Chemical Society, 2010 , vol. 132, # 35 p. 12216 - 12217]
Synthesis of 2-piperidinecarboxylic acid derivatives as potential anticonvulsants
[Ho, Bin; Venkatarangan, Prabha M.; Cruse, Sharon F.; Hinko, Christine N.; Andersen, Peter H.; Crider, Albert M.; Adloo, Ahmad A.; Roane, David S.; Stables, James P. European Journal of Medicinal Chemistry, 1998 , vol. 33, # 1 p. 23 - 31]
Straightforward entry to the pipecolic acid nucleus. Enantioselective synthesis of baikiain
[Ginesta, Xavier; Pericas, Miquel A; Riera, Antoni Tetrahedron Letters, 2002 , vol. 43, # 5 p. 779 - 782]
[Sanchez-Sancho, Francisco; Herradon, Bernardo Tetrahedron Asymmetry, 1998 , vol. 9, # 11 p. 1951 - 1965]