Water → Tert-butyl 3-(methanesulfonyloxy)pyrrolidine-1-carboxylate

Participants

Reaction Steps

To a solution of tert-butyl 3-hydroxypyrrolidine-1-carboxylate (Aldrich; 7.42 g, 39.6 mmol), in DCM (20 mL) was added, at 0° C., triethylamine (8.44 mL; 48.5 mmol) and then mesylchloride (3.13 mL; 40 mmol). The mixture was stirred for 18 hours at RT and then water was added and the product was extracted with DCM (3×20 mL). The combined organic fractions were dried (MgSO4), filtered and the solvent removed in vacuo to give tert-butyl 3-(methylsulfonyloxy)pyrrolidine-1-carboxylate (8.26 g; 77%) as a brown oil. 1H NMR: (CDCl3, 400 MHz) δ 5.27-5.20 (1 H, m), 3.70-3.49 (4 H, m), 3.04 (3 H, s), 2.90-2.05 (2 H, m), 1.46 (9 H, s).

Provenance & Evidence