Demethylation of (-)-1-(p-methoxybenzyl)-2-methyl-1,2,...

Details Demethylation of (-)-1-(p-methoxybenzyl)-2-methyl-1,2,... Demethylation of (-)-1-(p-methoxybenzyl)-2-methyl-1,2,...

C - Chemistry, Metallurgy

07

D

260/286

C07D 217/20 (2006.01) C07D 217/24 (2006.01) C07D 221/28 (2006.01) C07D 491/08 (2006.01)

Patent

CA 1109876

ABSTRACT N-Alkyl allylic tertiary amines are dealkylated as illustrated by treatment of (-)-1-(p-methoxybenzyl)-2- methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline in cold methylene chloride with m-chloroperbenzoic acid followed by the addition of aqueous ferrous chloride to provide a good yield of (+)-1-(p-methoxybenzyl)-1,2,3,4,5,6,7,8- octahydroisoquinoline with substantial if not complete retention of optical activity. The product is an inter- mediate in a synthesis of the analgesic known as butor- phanol.

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