反应详情

Ozone was bubbled through a −78° C. solution of 1-tert-butyl 4-methyl 4-allylpiperidine-1,4-dicarboxylate (4.0 g, 14.1 mmol) in 3:1 dichloromethane:methanol over 30 min to produce a blue solution. Nitrogen was bubbled through the reaction mixture for 30 min, then dimethylsulfide (5.2 mL, 70.6 mmol) was added and the reaction warmed to room temperature. After 3 h, the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of 5 to 50% ethyl acetate:hexane to give the title compound (1.72 g). MS: m/z 230.1 (M−tBu).

1. customNitrogen was bubbled through the reaction mixture for 30 min
2. concentrationthe reaction mixture was concentrated under reduced pressure
3. customThe crude product was purified by silica gel chromatography
4. washeluting with a gradient of 5 to 50% ethyl acetate