V. T. Mathad, G. B. Shinde, Sharad Subhash Ippar
Jan 13, 2011
Citations
0
Influential Citations
6
Citations
Journal
Synthetic Communications
Abstract
An efficient synthesis of 1-(naphthalen-1-yl)ethanamine ( RS -2) and its practical resolution to optically pure (1R)-(naphthalen-1-yl)ethanamine ( R -(+)-2), a key intermediate in the synthesis of cinacalcet hydrochloride (1), is described. The resolution of RS -2 using R-(−)-mandelic acid as a resolving agent in ethanol was established on an industrial scale to give pure R -(+)-2 with >99.8% ee after liberation of the amine from its mandelate salt. An efficient process for the racemization of undesired isomer S -(−)-2 is also provided to maximize the yield of desired enantiomer.