Trifluoroacetic acid → HCID 86660373, compound

Participants

Reaction Steps

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);

Provenance & Evidence