Coreximine and Related Compounds. II. : A Synthesis of (±)-Coreximine under Eschweiler-Clarke's Conditions : Studies on the Syntheses of Heterocyclic Compounds. CLXIII.

Abstract

1-(3-Benzyloxy-4-methoxybenzyl)-6-methoxy-7-benzyloxy-1, 2, 3, 4-tetrahydroisoquinoline (VI) and 1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-7-hydroxy-1, 2, 3, 4-tetrahydroisoquinoline (VII) were synthesized according to the route shown in Chart 1. VI and VII were reacted with formic acid or acetic acid to obtain respectively (±)-O, O-dibenzylcoreximine (IX) and (±)-coreximine (VIII). At the same time, (±)-norcoralydine (X) was prepared from (±)-norlaudanosine (XII) under the same condition and X was identified with (±)-norcoralydine derived from (±)-coreximine. Norcoralydine was found to occur in dimorphic forms of granular crystals (Xa) of m.p. 145∼145.5° and prismatic crystals (Xb) of m.p. 155°.