4-Toluenesulfonyl chloride → (1-Acetylpiperidin-4-yl)methyl 4-methylbenzenesulfonate

Participants

Reaction Conditions

Reaction Steps

Et3N (0.16 g, 1.60 mmol) and DMAP (0.39 g, 0.32 mmol) were added to a solution of methyl 4-(hydroxymethyl)piperidine-1-carboxylate (1.0 g, 3.20 mmol) in DCM (20 mL). The reaction mixture was cooled to 0° C. and TsCl (0.73 g, 3.80 mmol) was added. The reaction mixture was stirred for 1 h at room temperature, diluted with EtOAc, washed with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography (50% EtOAc:hexane) gave (1-acetylpiperidin-4-yl)methyl 4-methylbenzenesulfonate as a pale yellow semi-solid. Yield (1.2 g, 63%); 1H NMR (400 MHz, CDCl3); δ 7.77 (d, J=8.4 Hz, 2H), 7.63 (d, J=7.6 Hz, 2H), 4.64 (d, J=14.4 Hz, 2H), 3.92 (dd, J=6.0, 2.4 Hz, 2H), 3.84 (t, J=3.2 Hz, 4H), 3.02 (d, J=13.6 Hz, 2H), 2.54-2.49 (m, 2H), 2.45 (s, 3H), 1.72-1.62 (m, 1H), 1.16 (dt, J=12.4, 3.6 Hz, 1H); MS: m/z 312.05 [M+H]+.

Provenance & Evidence