Approach to the stereoselective synthesis of melatonin receptor agonist Ramelteon via asymmetric hydrogenation

…, M Yamashita, M Adachi, M Tanaka, K Matsumoto…

Index: Yamano, Toru; Yamashita, Masayuki; Adachi, Mari; Tanaka, Mitsutaka; Matsumoto, Kiyoharu; Kawada, Mitsuru; Uchikawa, Osamu; Fukatsu, Kohji; Ohkawa, Shigenori Tetrahedron Asymmetry, 2006 , vol. 17, # 2 p. 184 - 190

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Citation Number: 23

Abstract

Asymmetric synthesis of a novel non-benzodiazepine hypnotic drug Ramelteon (TAK-375) was accomplished via asymmetric hydrogenation. Development of the substrate design revealed that a novel class of substrate, allylic acylamine 4a, was hydrogenated with a Ru- BINAP catalyst in 95% ee and 98% yield. The effectiveness and robustness of the reaction were demonstrated on a 700-g scale.