Ozone → 1-(t-Butoxycarbonyl)-4-(t-butyldimethylsilyloxy)piperidin-3-one

Participants

Reaction Steps

To a solution of (E)-3-(2-acetoxyethylidene)-1-(t-butoxycarbonyl)-4-(t-butyldimethylsilyloxy)piperidine (9.9 g) in dichloromethane (100 ml) was introduced gaseous ozone at −78° C. for 2 hours. After the excess ozone was removed by bubbling nitrogen gas for 1 hour, triphenylphosphine (13 g) was added at the same temperature. The resulting mixture was stirred at room temperature for one hour, and concentrated in vacuo. The residue was purified by chromatography on silica gel using a mixture of hexane, ethyl acetate and dichloromethane (5:1:1 to 1:1:1) as the eluent to afford the title compound as a light yellow oil (4.6 g, yield: 56%).

Provenance & Evidence