1243166-48-4Relevant articles and documents
Efficient synthesis and practical resolution of 1-(naphthalen-1-yl) ethanamine, a key intermediate for cinacalcet
Mathad, Vijayavitthal T.,Shinde, Gorakshanath B.,Ippar, Sharad S.,Niphade, Navnath C.,Panchangam, Raghavendra K.,Vankawala, Pravinchandra J.
, p. 341 - 346 (2011)
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.