Methyl morpholine oxide → N-(5-Formylpyridin-2-yl)acetamide

Reaction equation

C[N+]1([O-])CCOCC1.[OH:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([NH:17][C:18](=[O:20])[CH3:19])=[N:15][CH:16]=1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH:10]([C:11]1[CH:12]=[CH:13][C:14]([NH:17][C:18](=[O:20])[CH3:19])=[N:15][CH:16]=1)=[O:9]

Participants

Procedure

500 mg of powdered molecular sieve (4 Å) and 113 mg (0.96 mmol) of N-methylmorpholine N-oxide are added to a solution of the crude product from example 18A in 2 ml of dry dichloromethane. 11 mg (0.03 mmol) of tetrapropylammonium perruthenate are then added to the reaction mixture, which is then stirred at RT for 1 h. The mixture is purified directly by chromatography on a silica gel fritte (mobile phase: gradient dichloromethane/ethanol 100:1→10:1). All product-containing fractions are combined, the solvent is removed on a rotary evaporator and the residue is purified further by another silica gel chromatography (mobile phase: gradient dichloromethane/ethanol 200:1→5:1).