Methanesulfonyl chloride → Tert-butyl 3-(methanesulfonyloxy)pyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 3-hydroxypyrrolidine-1-carboxylate (3.00 g, 16.02 mmol) was dissolved in dry DCM (50 mL) and cooled in an ice-water bath. Methanesulfonyl chloride (2.38 g, 20.83 mmol) was added followed by TEA (2.43 g, 24.03 mmol) and the reaction mixture was stirred at 0° C. for 3.5 h. The reaction mixture was washed with water (250 mL) and dried with MgSO4, filtered and evaporated. The crude product was purified using Biotage Horizon HPFC system (40+M column, isocratic run heptane/EtOAc (50:50)) affording the title compound (2.70 g, 63.5%). 1H NMR (500 MHz, CDCl3): δ 1.38 (s, 9H), 2.07 (bs, 1H), 2.18 (bs, 1H), 2.97 (s, 3H), 3.35-3.61 (m, 4H), 5.16-5.18 (m, 1H); 13C NMR (125 MHz, CDCl3): δ 28.59, 31.84, 32.76, 38.80, 43.61, 52.16, 80.12, 154.30.

Provenance & Evidence