Patent ID: 8729266

Claim:
A process for the preparation of a N-alkylated morphinan (II) having the formula the process comprising reducing an N-imine morphinan or hemiaminal morphinan in the presence of an asymmetric catalyst and a hydrogen source, wherein the asymmetric catalyst comprises a dichloro(arene)Ru(II) dimer and a N-tosyl-diphenylethylenediamine ligand, the N-imine morphinan or hemiaminal 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 6 is hydrogen, hydrocarbyl, substituted hydrocarbyl, or —OR 611 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 611 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 >NCH(OH)(R 9 ) or >N + ═CH(R 9 ); Z 2 is >NCH 2 (R 9 ); and R 9 is hydrogen, acyl, hydrocarbyl, substituted hydrocarbyl, or heterocyclo.