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Paper | Regular issue | Vol 71, No. 2, 2007, pp.323-330
Published online, 22nd December, 2006
DOI: 10.3987/COM-06-10926
Practical Synthesis of (-)-α-Aminobenzolactam via Nitration-Cyclization of L-Homophenylalanine Ethyl Ester

Luoting Yu, Jiling Huang, Ching-Yao Chang, and Teng-Kuei Yang*

*Wisdom Pharmaceutical Co.Ltd., Haimen, Jiangsu, 226100, China

Abstract

A practical synthesis of chiral (-)-α-aminobenzolactam (2) is described. The target compound (2) was prepared from commercially available L-homophenylalanine ethyl ester hydrochloride (LHPE·HCl 1) with a highly enantiomeric purity (>98% e.e.) by employing simple nitration and hydrogenation-cyclization reactions.