Synthesis of derivatives of codeine and other 3-O-alkylmorphines

Details Synthesis of derivatives of codeine and other 3-O-alkylmorphines Synthesis of derivatives of codeine and other 3-O-alkylmorphines

1986-12-24

1989-01-03

Daus, Donald G.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546 44, C07D48908

Patent

active

047958138

ABSTRACT:
A 14-hydroxy group is introduced into a morphinan structure by singlet oxygen reaction with a novel dienol ester of an N-substituted-3-O-alkylnormorphinone. The resultant N-substituted-3-O-alkyl-141-hydroxynormorphinone is also a novel compound which may be catalytically hydrogenated to produce a novel N-substituted-3-O-alkylnoroxymorphone. The latter intermediate may be converted to a 3-O-alkylnoroxymorphone by hydrolytic removal of the N-substituent and to noroxymorphone by both hydrolysis and O-dealkylation.
The dienol ester intermediate is prepared by N-demethylation of codeine or other 3-O-alkylmorphine by reaction with a cyanogen halide or haloformate ester, followed by oxidation of the resultant N-substituted-3-O-alkylnormorphine to an N-substituted-3-O-alkylnormorphinone and esterification of the latter with an acid anhydride or acid halide.

REFERENCES:
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patent: 4241065 (1980-12-01), Boswell, Jr. et al.
patent: 4639520 (1987-01-01), Kavka
Gutsche, et al., "Fundamentals of Organic Chemistry", pp. 121, 390 and 471 1975).
Fieser, et al., "Advanced Organic Chemistry", p. 34 (1961).
Von Nostrand Chemist's Dictionary, Honig, et al., ed., p. 506 (1953).
Bentley, The Chemistry of the Morphine Alkaloids, Oxford at the Clarendon Press (1954), p. 252.
McOmie, Protective Groups in Organic Chemistry, Plenum Press, London & New York, 1973, p. 56.

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