Process for the preparation of 14-hydroxymorphinans

Details Process for the preparation of 14-hydroxymorphinans Process for the preparation of 14-hydroxymorphinans

1975-07-31

1976-09-14

Gotts, Lewis

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260285, 26032611R, 260566R, 260566F, 2605705CA, 260590FA, 260613R, C07D20944

Patent

active

039806413

ABSTRACT:
N-substituted-14-hydroxy-3-substituted-morphinan derivatives have been found to possess potent narcotic agonist or antagonist activity. In particular, the compound 3,14-dihydroxy-N-cyclopropylmethylmorphinan has been found to possess potent agonist-antagonist activity. A new and more efficient total synthesis for the preparation of these compounds is described herein, which improvement comprises using a Schiff base of 4a-(2-aminoethyl)-1,2,3,4,4a,9-hexahydro-6-methoxyphenanthrene to produce 3-methoxy-9-bromo-norhasubanan hydrobromide in substantially improved yields through the intermediate of the formula ##SPC1##

REFERENCES:
patent: 3166599 (1965-01-01), Sawa et al.
patent: 3775414 (1973-11-01), Monkovic et al.
patent: 3819635 (1974-06-01), Pachter et al.
Sawa et al., Tetrahedron, vol. 24, pp. 6185-6196 (1968).

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