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Communication | Regular issue | Vol 20, No. 10, 1983, pp.1945-1950
Published online, 1st January, 1970
DOI: 10.3987/R-1983-10-1945
A Facile Synthesis of 4-Aryl-1,2,3,4-tetrahydroisoquinolines: A Total Synthesis of (±)-Cherylline

Hiroshi Hara, Ryuichi Shirai, Osamu Hoshino, and Bunsuke Umezawa

*Faculty of Pharmaceutical Sciences, Science University of Tokyo, 2641 Yamazaki, Noda, Chiba 278-8510, Japan

Abstract

Reaction of benzylamines (3a-d) and styrene oxide at 140 °C gave quantitatively β-hydroxyphenethylamine (2a-d), acid treatment of which afforded 4-aryl-1,2,3,4-tetrahydroisoquinolines (8a-d) in high yields. On the other hand, the styrene oxide (10 or 15) was treated with BF3-Et2O in MeOH yielding regioselectively a β-methoxyphenethyl alcohol (12 or 16), the mesylate of which reacted with the benzylamine (3e) in the presence of Hünig’s base to give the N-benzyl-β-methoxyphenethylamine (2f or 2g). Acid treatment of 2f or 2g afforded (±)-cherylline (1) or (±)-4’-O-methylcherylline (14) in 85 or 67% overall yield from O-benzylisovanillin.