Triethylamine → (S)-1-(4-chlorobenzyl)-2-oxopyrrolidin-3-yl methanesulfonate

Participants

Reaction Conditions

Reaction Steps

Triethylamine (0.825 mL, 5.92 mmol) and methansulfonyl chloride (0.338 mL, 4.34 mmol) was added to a stirred solution of (S)-1-(4-chlorobenzyl)-3-hydroxypyrrolidin-2-one (890 mg, 3.94 mmol) in dichloromethane (20 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 h. The resulting mixture was diluted with water and the aqueous mixture was extracted with dichloromethane. The combined organic layers were washed with 10% sodium bicarbonate solution, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was purified using silica gel column chromatography (0-100% EtOAc). The pure fractions were combined and concentrated in vacuo to afford (S)-1-(4-chlorobenzyl)-2-oxopyrrolidin-3-yl methanesulfonate (1.1 g, 3.62 mmol, 92% yield) as a white solid: LC-MS (M+H)+ 304.1; 1H NMR (500 MHz, chloroform-d) δ 7.38-7.33 (m, 2H), 7.22-7.17 (m, 2H), 5.25 (dd, J=8.2, 7.6 Hz, 1H), 4.52-4.41 (m, 2H), 3.40-3.31 (m, 4H), 3.25 (dt, J=10.0, 7.3 Hz, 1H), 2.58 (dddd, J=13.7, 8.4, 7.5, 3.3 Hz, 1H), 2.33-2.20 (m, 1H).

Provenance & Evidence