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Note | Regular issue | Vol 55, No. 3, 2001, pp.589-595
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9151
Bischler-Napieralski Cyclization of N-[2- (2-Bromo-5-hydroxy-4-methoxyphenyl)ethyl]-N-[(S)-1-phenylethyl]-2-(2-bromo-4,5-dimethoxyphenyl)acetamide Accompanied by Elimination of Chiral Auxiliary

Kumiko Miyatani, Mariko Ohno, Kazuyo Tatsumi, Yoshitaka Ohishi,* Jun-ichi Kunitomo, Ikuo Kawasaki, Masayuki Yamashita, and Shunsaku Ohta

*Faculty of Pharmaceutical Science, Mukogawa-Women's University, 11-68 Koushien Kyuban-Cho, Nishinomiya, Hyogo 663-8179, Japan

Abstract

N-[2-(2-bromo-5-hydroxy-4-methoxyphenyl)ethyl]-N-[(S)-1-phenylethyl]-2-(2-bromo-4,5-dimethoxyphenyl)acetamide (5) was cyclized under N-dealkylation at the 2-position to the racemic 1-benzyl-1,2,3,4-tetrahydroisoquinoline derivatives (6) by the Bischler-Napieralski cyclization followed by NaBH4 reduction (Polniaszek’s method).