Methyl morpholine oxide → 3-Benzyl-3-azabicyclo[3.2.1]octan-6-one

Participants

Reaction Conditions

Reaction Steps

A solution of 3-benzyl-3-aza-bicyclo[3.2.1]octan-6-ol (8 mmol) in anhydrous dichloromethane at 0° C. under nitrogen was treated with of N-methyl morpholine N-oxide (12 mmol), 1 weight equivalent of oven dried 4 angstrom sieves and TPAP (tetrapropylammonium perruthenate) (0.2 mmol). The reaction mixture was stirred for 30 min. at 0° C. then allowed to warm to room temperature with stirring for an additional 1 h. The reaction was filtered through a plug of silica gel and eluted with ethyl acetate then striped to an oil. Purification by silica gel chromatography eluted with 15% ethyl acetate/hexanes produced an oil (7.7 mmol). APCl MS m/z 216.2 (M+H)+.

Provenance & Evidence