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

1977-02-17

1979-02-13

Daus, Donald G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546 91, 546142, 546146, C07D22128, C07D21724

Patent

active

041395344

ABSTRACT:
N-substituted-14-hydroxy-3-substituted-morphinan derivatives have been found to possess potent narcotic agonist or antagonist activity. In particular, the compound N-Cyclobutylmethyl-3,14-dihydroxymorpinan has been found to posess potent agonist/antagonist activity as a non-narcotic analgesic. An improved total snythesis 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)perhydroisoquinolin e (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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patent: 4058531 (1977-11-01), Monkovic et al.
Fieser et al., Reagents for Organic Synthesis, John Wiley & Sons, N.Y., p. 202, 1967.
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Schnider et al., Helv. Chim Acta 34 2218-2222 (1951).
Schnider et al., Helv. Chim Acta 376 710-720 (1954).
Schnider et al., Helv. Chim Acta 33, 1437-1448 (1950).

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