Potassium Carbonate → tert-Butyl 3-(4-bromophenylthio)piperidine-1-carboxylate

Participants

Reaction Steps

A mixture of 4-bromobenzenethiol (4.697 g, 24.84 mmol), tert-butyl 3-methylsulfonyloxypiperidine-1-carboxylate (6.939 g, 24.84 mmol) and K2CO3 (6.866 g, 49.68 mmol) in DMF (40 mL) were stirred at ambient temperature for 16 hours. The reaction mixture was cooled to 0° C. and diluted with water. The reaction mixture was extracted with ethylacetate (×2) and the combined organic extracts washed with saturated aqueous sodium thiosulphate solution (×2), water (×2), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion, 330 g eluting with 0 to 50% Et2O/Petroleum Ether, loaded in DCM) to give tert-butyl 3-((4-bromophenyl)thio)piperidine-1-carboxylate as a colourless oil (1.68 g, 18% Yield). H NMR (400.0 MHz, CDCl3) δ 0.97-0.86 (m, 2H), 1.44 (s, 9H), 1.80-1.76 (m, 1H), 2.12-2.08 (m, 1H), 2.92-2.86 (m, 1H), 3.14-3.08 (m, 2H), 3.89 (br d, 1H), 4.05 (br s, 1H), 7.30 (d, 2H) and 7.45-7.43 (m, 2H) ppm;

Provenance & Evidence