One-Pot Racemization Process of 1-Phenyl-1, 2, 3, 4-tetrahydroisoquinoline: A Key Intermediate for the Antimuscarinic Agent Solifenacin

…, M Pallavicini, L Fumagalli, V Straniero…

Index: Bolchi, Cristiano; Pallavicini, Marco; Fumagalli, Laura; Straniero, Valentina; Valoti, Ermanno Organic Process Research and Development, 2013 , vol. 17, # 3 p. 432 - 437

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Citation Number: 14

Abstract

(S)-(+)-1-Phenyl-1, 2, 3, 4-tetrahydroisoquinoline, which is the key intermediate in preparing the urinary antispasmodic drug solifenacin, was racemized in quantitative yield by a simple one-pot procedure through N-chlorination with trichloroisocyanuric acid, conversion of the N- chloroamine into the imine hydrochloride, and reduction of the imine double bond. The racemized amine was successfully resolved by d-(−)-tartaric acid obtaining (S)-1-phenyl-1 ...