Process for the preparation of 3, 14.beta.-dihydroxy-17-normorph

Details Process for the preparation of 3, 14.beta.-dihydroxy-17-normorph Process for the preparation of 3, 14.beta.-dihydroxy-17-normorph

1994-07-22

1996-04-02

Rotman, Alan L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

514289, C07D22128

Patent

active

055042082

ABSTRACT:
Process for the preparation of 3,14.beta.-dihydroxy-17-normorphinan ##STR1## A suitable economic process for the preparation of 3,14.beta.-dihydroxy-17-normorphinan of a general formula (I) is being solved, which is a key intermediate of a semisynthetic synthesis of an effective analgesic of Butorphanol from thebaine.
Synthesis includes a two step N-demethylation, and concerted dephenoxylation of 4-phenoxy-14.beta.-hydroxy-3-methoxymorphinan in the first step by means of a chloroformate, then, in the second step, by means of sodium action in a liquid ammonia, and by means of the following O-demethylation under action of a complex of aluminium chloride - dialkylsulfide.

REFERENCES:
patent: 3819635 (1974-06-01), Pachter et al.
Article-Ceskoslov, Fram. 32, 1983, No. 1, pp. 23-26.

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