5-[(Benzylamino)methyl]cyclohex-2-en-1-ol → 6-Benzyl-6-azabicyclo[3.2.1]octan-3-one

Participants

Reaction Steps

To a solution of 5-(benzylaminomethyl)cyclohex-2-enol (3.80 g, 17.5 mmol) in dry dichloromethane (150 ml) was added activated manganese dioxide (18.0 g, 210 mmol) in one portion. The mixture was stirred vigorously under nitrogen for 2 h. The yellow solution was filtered through Celite and the solids were washed with dichloromethane (2×50 ml). The combined filtrates were concentrated by rotary evaporation to give an orange oil, which solidified on brief standing. The solid was recrystallized from hot hexane/ether to afford the ketone as an off-white solid (2.6 g, 68%).

Provenance & Evidence