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

rac-3-Methoxy-6-oxo-N-methylmorphinan was synthesized from 1-(p-methoxybenzyl)-2-methyl-6-oxo-Δ9, 10-octahydroisoquinoline and also from 1-(p-methoxybenzyl)-2-methyl-6-oxo-Δ5, 10-octahydroisoquinoline by the action of 85% phosphoric acid according to Grewe's cyclization, respectively. 1-(p-Methoxybenzyl)-2-methyl-6, 6-ethylenedioxy-Δ9, 10-octahydroisoquinoline, which was used as a starting material, was prepared from 2-(p-methoxybenzyl)-2-methyl-6, 6-ethylenedioxy-Δ9, 10-octahydroisoquinolinium chloride by means of Stevens'rearrangement.