Triethylamine → (3S)-1-(methylsulfonyl)pyrrolidin-3-yl methanesulfonate

Participants

Reaction Steps

To a dichloromethane (200 mL) solution of (S)-3-hydroxypyrrolidine (5.0 g, 57 mmol) and triethylamine (24.0 mL, 172 mmol) at 0° C. was added methanesulfonyl chloride (7.23 g, 63.1 mmol). 4-(Dimethylamino)pyridine (0.70 g, 5.7 mmol) was then added, and the mixture was stirred at room temperature for 2 hours. It was diluted with dichloromethane (50 mL), and the combined organic layers were washed with aqueous 1 M hydrochloric acid (30 mL), water (30 mL), brine (30 mL), dried (magnesium sulfate), filtered and concentrated in vacuo to afford the title compound. The crude product was used in the subsequent step without further purification. 1H NMR (500 MHz, CDCl3) δ 5.28 (t, J=4.5 Hz, 1H), 3.71 (d, J=12.9 Hz, 1H), 3.64 (dd, J=12.7, 4.0 Hz, 1H), 3.59 (td, J=9.2, 2.3 Hz, 1H), 3.46 (td, J=10.1, 6.7 Hz, 1H), 3.07 (s, 3H), 2.89 (s, 3H), 2.39-2.33 (m, 1H), 2.29-2.19 (m, 1H); LC-MS: m/z 244.1 (M+H).

Provenance & Evidence