A new selective oxidation of N-methyl to N-formyl upon threo-(1S,2S)2-(N, N-dimethylamino)-1-(4′-nitrophenyl)-1,3-propanediol

A new chemoselective oxidation of N-methyl to N-formyl upon threo-(1S,2S)-2-(N,N-dimethylamino)-1-(4'-nitrophenyl)-1,3-propanediol was reported. In the presence of Na2HPO4, threo-(1S,2S)-2-(N,N-dimethylamino)-1-(4'-nitrophenyl)-1,3-propanediol (DMANP) was oxidized by a 717 anion exchange resin-supported bromine in a H2O-CCl4 system at 60 degreesC for 24 h to give threo-(1S, 2S)-2-(N-formyl-N-methylamino)-1-(4'-nitrophenyl) -1, 3-propanediol ( FMANP) in 51% yield. This selective oxidation of N-methyl to N-formyl was observed for the first time in 2-amino-1,3-propanediol derivative chemistry.