Selective C–N bond oxidation: demethylation of N-methyl group in N-arylmethyl-N-methyl-α-amino esters utilizing N-iodosuccinimide (NIS)

Abstract Demethylation of N -methyl group in N -methyl- N -arylmethyl-α-amino esters was accomplished by the oxidation of the amino group using the N -iodosuccinimide (NIS)/acetonitrile system followed by treatment with O -methylhydroxylamine hydrochloride. This combination of reagents could provide a complementary method to catalytic hydrogenolysis, which certainly cleaves N -arylmethyl groups, in organic synthesis.