Chloroacetyl chloride → (S)-1-(chloroacetyl)-2-pyrrolidinemethanol

Participants

Reaction Steps

A solution of chloroacetyl chloride, 27.7 g (0.247 mol), in 66.5 ml of acetone is added dropwise with stirring to a solution of 25 g (0.247 mol) of L-prolinol and 40.4 g (0.493 mol) of sodium acetate in a mixture of 400 ml of acetone and 200 ml of water at 0°-5° C. The mixture is stirred and allowed to reach room temperature over two hours, the solvent is evaporated in vacuo and the residue is suspended in 300 ml chloroform and washed with water, 2×300 ml. The chloroform layer is separated, dried over sodium sulfate, evaporated in vacuo and the residue is purified by chromatography using silica gel and eluting with dichloromethane-methanol (98:2) to give (S)-1-(chloroacetyl)-2-pyrrolidinemethanol, 34.1 g; [α]D25 -62.2° (c 1.00, methanol).

Provenance & Evidence