Potassium Carbonate → Tert-butyl 4-[(4-nitrophenyl)sulfanyl]piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Potassium carbonate (0.45 g, 3.5 mmol) was added in one portion to a stirred solution of 4-methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl ester (0.75 g, 2.5 mmol) and 4-nitrothiophenol (0.5 g, 3.2 mmol) in DMF (25 ml) and the mixture heated to 70° C. for 7 hours. After this time, the reaction mixture was concentrated under vacuum and re-dissolved in ethyl acetate (25 ml) and washed with NaOH (1M solution, 20 ml) and brine (20 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated under vacuum. The resulting residue was purified by column chromatography (elution: 60% heptane, 40% ethyl acetate) to afford the title compound (0.74 g, 68% yield) as an off-white solid. δH (250 MHz, DMSO) 8.14 (2H, d), 7.55 (2H, d), 3.89-3.69 (3H, m), 3.07-2.90 (2H, m), 2.04-1.89 (2H, m), 1.51-1.33 (10H, m).

Provenance & Evidence