Author： Mathad Vijayavitthal Shinde Gorakshanath Ippar Sharad Niphade Navnath Panchangam Raghavendra Vankawala Pravinchandra
Publisher： Taylor & Francis Ltd
ISSN： 0039-7911
Source： Synthetic Communications, Vol.41, Iss.3, 2011-01, pp. : 341-346
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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.
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