Synthetic Communications p. 341 - 346 (2011)
Update date:2022-09-26
Topics:
Mathad, Vijayavitthal T.
Shinde, Gorakshanath B.
Ippar, Sharad S.
Niphade, Navnath C.
Panchangam, Raghavendra K.
Vankawala, Pravinchandra J.
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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