Patent ID: 7985858

Claim:
A process for the preparation of a 6-hydroxy morphinan (II) having the formula the process comprising reducing a 6-keto morphinan (I) in the presence of a ruthenium, rhodium, or iridium asymmetric catalyst and a hydrogen source, the 6-keto morphinan (I) 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 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 1 is >N(R 9 ), >N + (R 9 )(R 10 ), >NCH(OH)(R 9 ), or >N + ═CH(R 9 ); Z 2 is (i) Z 1 when Z 1 is >N(R 9 ) or >N + (R 9 )(R 10 ); or (ii) >NCH 2 (R 9 ) when Z 1 is >NCH(OH)R 9 or >N + ═CH(R 9 ); and R 9 and R 10 are independently hydrogen, acyl, hydrocarbyl, substituted hydrocarbyl, or heterocyclo.