Process for the preparation of 14-hydroxymorphinan derivatives

Details Process for the preparation of 14-hydroxymorphinan derivatives Process for the preparation of 14-hydroxymorphinan derivatives

C - Chemistry, Metallurgy

07

D

260/237.69

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

Patent

CA 1086723

ABSTRACT OF THE DISCLOSURE N-substituted -14-hydroxy-3-substituted-morphinan derivatives have been found to possess potent narcotic agonist or antagonist activity. In particular, the compound N-Cyclo- butylmethyl-3,14-dihydroxymorpinan has been found to possess potent agonist/antagonist activity as a non-narcotic analgesic. An improved total synthesis of these compounds is described herein from the starting material 2-(p-methoxybenzyl)-1,2,3,4, 5,6,7,8-octahydroisoquinoline. A preferred feature of the process involves borane reduction of 2-cyclobutylcarbonyl-9,10- dihydroxy-1-(p-methoxybenzyl) perhydroisoquinoline (Va) to provide the corresponding cyclobutylmethyl derivative complexed with borane which is converted directly to N-cyclobutylmethyl-14.beta.- hydroxy-3-methoxymorphinan (LVa) by treating with acid.

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