Patent ID: 8524904

Claim:
A process wherein a 6-hydroxy morphinan (II) is reacted to form a 6-hydroxy-N-alkylated morphinan (III) having the formula: the process comprising reacting the 6-hydroxy morphinan (II) with an aldehyde of the formula CH(O)R 9 in a solvent, followed by reducing with a hydride reducing agent, the 6-hydroxy morphinan (II) having the formula: wherein R 1 is hydrogen, hydrocarbyl, substituted hydrocarbyl, halo, or —OR 111 ; R 2 is hydrogen, hydrocarbyl, substituted hydrocarbyl, halo, or —OR 211 ; R 3 is hydrogen, hydrocarbyl, substituted hydrocarbyl, or —OR 311 ; R 7 is hydrogen, hydrocarbyl, substituted hydrocarbyl, or —OR 711 ; R 8 is hydrogen, hydrocarbyl, substituted hydrocarbyl, or —OR 811 ; R 9 is hydrogen, acyl, hydrocarbyl, substituted hydrocarbyl, or heterocyclo; R 14 is hydrogen or hydroxy; R 111 is hydrogen, hydrocarbyl, substituted hydrocarbyl, or a hydroxy protecting group; R 211 is hydrogen, hydrocarbyl, substituted hydrocarbyl, or a hydroxy protecting group; R 311 is hydrogen, hydrocarbyl, substituted hydrocarbyl, or a hydroxy protecting group; R 711 is hydrogen, hydrocarbyl, substituted hydrocarbyl, or a hydroxy protecting group; R 811 is hydrogen, hydrocarbyl, substituted hydrocarbyl, or a hydroxy protecting group; Z 2 is >NH; and Z 3 is >NCH 2 (R 9 ), wherein the 6-hydroxy morphinan (II) and the 6-hydroxy-N-alkylated morphinan (III) have a 6-alpha-hydroxy moiety.