Chloroacetyl chloride → (5S)-1-(Chloroacetyl)-5-methyl-L-prolinamide

Participants

Reaction Conditions

Reaction Steps

(2S,5S)-5-Methyl-pyrrolidine-2-carboxylic acid amide trifluoroacetate (2.0 g, 8.2 mmol, Example 84D) and triethyl amine (1.9 mL, 24.6 mmol) were dissolved in CH2Cl2 (6 mL), and the mixture was cooled to 0° C. Chloroacetyl chloride (0.39 mL, 9.0 mmol) was added slowly via syringe. After 2 h, saturated NaHCO3 was added, and the mixture was extracted with EtOAc (3×). The combined organic extracts were dried (Na2SO4), concentrated and purified by flash chromatography (10% MeOH/EtOAc) to give the title compound. MS (DCI) m/z 205 (M+H)+.

Provenance & Evidence