Study on the Synthesis of rac-3-Methoxy-6-oxo-N-methylmorphinan

Abstract

rac-3-Methoxy-6-oxo-N-methylmorphinan was synthesized from 1-(p-methoxybenzyl)-2-methyl-6-oxo-Δ^{9, 10}-octahydroisoquinoline and also from 1-(p-methoxybenzyl)-2-methyl-6-oxo-Δ^{5, 10}-octahydroisoquinoline by the action of 85% phosphoric acid according to Grewe's cyclization, respectively. 1-(p-Methoxybenzyl)-2-methyl-6, 6-ethylenedioxy-Δ^{9, 10}-octahydroisoquinoline, which was used as a starting material, was prepared from 2-(p-methoxybenzyl)-2-methyl-6, 6-ethylenedioxy-Δ^{9, 10}-octahydroisoquinolinium chloride by means of Stevens'rearrangement.