Studies on the Syntheses of Heterocyclic Compounds. CLXXXVII : Optical Resolution of dl-7-O-Benzylcoclaurine

Abstract

dl-7-O-Benzylcoclaurine (V), which had never been optically resolved, was synthesized by cyclization of the amide (III), obtained by the usual method, and subsequent reduction. Optical resolution of V was effected by the use of bis(p-toluoyl)-d-and-l-tartaric acid. Dextrorotatory V, m.p. 184∼186°, was obtained from d-7-O-benzylcoclaurine bis (p-toluoyl)-d-tartrate, m.p.184∼186°, and l-7-O-benzylcoclaurine (levorotatory V), m.p. 184∼186°, from the l-tartrate, m.p. 134.5∼136.5°.