Patent ID: 8269006

Claim:
A process for the preparation of a N-alkylated ketomorphinan compound of Formula (IV): the process comprising: maintaining a ketone group of a N-imine ketomorphinan or hemiaminal ketomorphinan as unprotected; and, reducing the N-imine ketomorphinan or hemiaminal ketomorphinan in the presence of a hydrogen source and a catalyst without substantially reducing the 6-keto functionality to an alcohol, the N-imine ketomorphinan or hemiaminal ketomorphinan compound of Formula (III): wherein: R 1 , and R 2 are independently selected from the group consisting of hydrogen, hydrocarbyl, substituted hydrocarbyl, halo, and {—}OR 15 ; R 3 , R 7 , and R 8 are independently selected from the group consisting of hydrogen, hydrocarbyl, substituted hydrocarbyl, and {—}OR 15 ; R 9 is selected from the group consisting of hydrogen, acyl, hydrocarbyl, substituted hydrocarbyl, and heterocyclo; R 14 is selected from the group consisting of hydrogen and hydroxy; R 15 is selected from the group consisting of hydrogen, hydrocarbyl, substituted hydrocarbyl, and a hydroxy protecting group; X is oxygen; Z 1 is selected from the group consisting of {—}NCH(OH)(R 9 ), and {—}N + ═CH(R 9 ); and Z 2 is {—}NCH 2 R 9 .