Chloroacetyl chloride → 2-Pyrrolidinemethanol, 1-(chloroacetyl)-, (2S)-

Participants

Reaction Conditions

Reaction Steps

To a solution of 2(S)-hydroxymethylpyrrolidine (25.32 g, 250.3 mmol) in CH2Cl2 (720 mL) under argon was added Et3N (38.0 mL, 273 mmol). After cooling this mixture to -20° C., chloroacetyl chloride (20.0 mL, 251 mmol) was added dropwise over 0.75 h maintaining the reaction temperature at -20 ±3° C. The reaction was stirred at ambient temperature for 18 h and evaporated in vacuo. An impurity which precipitated during concentration was removed by filtration. The crude product was purified by chromatography (silica gel, 1:39 to 1:19 MeOH/CH2Cl2) to give the title compound as a yellow oil. 1H NMR (CDCl3, 400 MHz): δ4.37 (dd, J=8, 3 Hz, 1H), 4.22 (qd, J=7, 3 Hz, 1H), 4.08 (s, 2H), 3.71 (td, J=8, 3 Hz, 1H), 3.68-3.50 (m, 3H), 2.14-1.86 (m, 3H), 1.72-1.62 (m, 1H).

Provenance & Evidence