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

Temperature

-20 °C

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).

1. temperaturemaintaining the reaction temperature at -20 ±3° C
2. customevaporated in vacuo
3. customAn impurity which precipitated during concentration
4. customwas removed by filtration
5. customThe crude product was purified by chromatography (silica gel, 1:39 to 1:19 MeOH/CH2Cl2)

ORD record

ord-3e3ea3c0157d43ef8bc6e10fc6e5b18e

Source dataset

uspto-grants-1999_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05872135