Patent ID: 6887998

Claim:
A process for converting a phenolic 3-hydroxyl on a morphinane of structure wherein R 2 and R 2a are both hydrogen or taken together R 2 and R 2a are â•O; R 3 is chosen from hydrogen, lower alkyl, alkenyl, benzyl, aryl, heterocyclyl and hydroxyalkyl; R 4 is chosen from hydrogen, hydroxy, amino, lower alkoxy, C 1 -C 20 alkyl and C 1 -C 20 alkyl substituted with hydroxy or carbonyl; R 9 is hydrogen or lower alkyl; R 10 is chosen from hydrogen, lower alkyl and hydroxy(lower alkyl); or together, R 9 and R 10 form a spiro-fused carbocycle of 5 to 10 carbons; R 11 is hydrogen; R 12 is chosen from hydroxy, lower alkoxy, â€”NH 2 , â€”N(CH 2 CH 2 Cl) 2 , and â€”NHC(O)CHâ•CHCOOCH 3 ; or together, R 11 and R 12 form a carbonyl or a vinyl substituent; to a thiocarboxamide comprising: (a) reacting said phenolic hydroxyl with a reagent to convert said phenolic hydroxyl to a group displaceable by CN âŠ– ; (b) reacting said group displaceable by CN âŠ– with Zn(CN) 2 in the presence of a Pd(0) catalyst to provide a nitrile; (c) hydrolyzing said nitrile to a carboxamide; and (d) reacting said carboxamide with a pentavalent phosphorus-sulfur reagent.