Synthesis of derivatives of codeine and other 3-0-...

Details Synthesis of derivatives of codeine and other 3-0-... Synthesis of derivatives of codeine and other 3-0-...

C - Chemistry, Metallurgy

07

D

204/91.17, 260/2

C07D 489/02 (2006.01) C07D 489/08 (2006.01)

Patent

CA 1198423

SYNTHESIS OF DERIVATIVES OF CODEINE AND OTHER 3-0-ALKYLMORPHINES Abstract of the Invention A 14-hydroxy group is introduced into a morphinan structure by singlet oxygen reaction with a novel dienol ester of an N-substituted-3-0-alkylnormorphinone. The resultant N-substituted-3-0-alkyl-14-hydroxynormorphinone is also a novel compound which may be catalytically hydrogenated to produce a novel N-substituted-3-0-alkylnoroxymorphone. The latter intermediate may be converted to a 3-0-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 3-0-alkylmorphine by reaction with a cyanogen halide or haloformate ester, followed by oxidation of the resultant N-substituted-3-0-alkylnormorphine to an N-substituted-3-0-alkylnormorphinone and esterification of the latter with an acid anhydride or acid halide.

409500

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