Syntheses of dl-7, 4'-O, O-Dibenzyl-3'-bromo-N-methylcoclaurine and Its Optical Resolution : Studies on the Syntheses of Heterocyclic Compounds. CLIII.

Abstract

One of the important starting materials for biscoclaurine-type alkaloids, dl-3'-bromo-7, 4'-O, O-dibenzyl-N-methylcoclaurine (III) was synthesized through its amide (VIII), 3, 4-dihydroisoquinoline (IX), and the methiodide (X). Optical resolution of III using di- p-toluoyl-d-tartaric acid gave the levorotatory III. The dextrorotatory III was obtained from the free base recovered from the mother liquor by treatment with l-tartaric acid.