Triethylamine → Tert-butyl (3R)-3-(methanesulfonyloxy)pyrrolidine-1-carboxylate

Participants

Reaction Steps

A solution of (R)-3-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester (0.500 g, 2.67 mmol) in DCM (6.7 mL) was cooled to 0° C. and charged with triethylamine (0.45 mL, 3.20 mmol), methanesulfonyl chloride (0.23 mL, 2.90 mmol), and 4-dimethylaminopyridine (3.0 mg, 0.03 mmol) and stirred at rt for 6 h. The reaction mixture was partitioned between CHCl3 and sat. NaHCO3 and separated. The aqueous was re-extracted with CHCl3 (3×) and the combined organic fractions were washed with sat. NaHCO3 (2×), brine (2×), dried over Na2SO4, filtered and concentrated in vacuo resulting in the title compound as a pale yellow oil. This material was taken on to the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 1.47 (s, 9H), 2.06-2.39 (m, 2H), 3.05 (s, 3H), 3.38-3.82 (m, 4H), 5.27 (t, J=4.4 Hz, 1H).

Provenance & Evidence