Efficient Synthesis and Practical Resolution of 1-(Naphthalen-1-yl)ethanamine,a Key Intermediate for Cinacalcet |
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| Authors: | Vijayavitthal T. Mathad Gorakshanath B. Shinde Sharad S. Ippar Navnath C. Niphade Raghavendra K. Panchangam Pravinchandra J. Vankawala |
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| Affiliation: | 1. Department of Process Research and Development, Megafine Pharma (P) Ltd. , Nashik, Maharashtra, India drvtmathad@yahoo.co.in;4. vt.mathad@megafine.in;5. Department of Process Research and Development, Megafine Pharma (P) Ltd. , Nashik, Maharashtra, India |
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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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| Keywords: | Cinacalcet industrially feasible 1-(naphthalen-1-yl)ethanamine R-(?)-mandelic acid resolution |
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