Dimethyl Sulfide → 1-Tert-butyl 4-methyl 4-(2-oxoethyl)piperidine-1,4-dicarboxylate

関与物質

反応手順

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).

情報源と証拠