4-(cyclopropylmethylsulfonyl)piperidine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To an ice-cold solution of tert-butyl 4-(cyclopropylmethylsulfonyl)piperidine-1-carboxylate (53, 0.9 g, 2.96 mmol) in CH2Cl2 (15 mL) was added TFA (3.0 mL). The mixture stirred at room temperature and stirred for 3 h and was concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (25 mL) and the organic layer was washed with saturated NaHCO3 solution (10 mL), H2O (15 mL) brine (15 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was chromatographed over silica gel (Isco CombiFlash Companion unit, 40 g Redisep column, 30% to 50% EtOAc in hexanes) to give 4-(cyclopropylmethylsulfonyl)piperidine as a white foam (54, 0.38 g, 63%); 1H NMR (300 MHz, MeOH-d4): δ 3.27-3.24 (m, 1H), 3.23-3.12 (m, 2H), 2.99 (d, J=7.2 Hz, 2H), 2.63 (dt, J=2.4, 12.0 Hz, 2H), 2.10-2.01 (m, 2H), 1.77-1.60 (m, 2H), 1.27-1.14 (m, 1H), 0.83-0.64 (m, 2H), 0.45-0.39 (m, 2H); stirred for 3 h was concentrated under reduced pressure The residue was dissolved in CH2Cl2 (25 mL) the organic layer was washed with saturated NaHCO3 solution (10 mL), H2O (15 mL) brine (15 mL) dried over Na2SO4 filtered concentrated under reduced pressure The residue was chromatographed over silica gel (Isco CombiFlash Companion unit, 40 g Redisep column, 30% to 50% EtOAc in hexanes)