Chloroacetyl chloride → HCID 14143058, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2S)-2-[(phenylmethyl)amino]-1-propanol (10.52 g, 63.67 mmol) in THF (65 mL) was added a solution of K2CO3 (26.40 g, 191.0 mmol) in water (65 mL). The vigorously stirred mixture was cooled to 0° C., and chloroacetyl chloride (7.10 mL, 89.14 mmol) was added dropwise over 20 min. The mixture was stirred for 1 h, and then an additional portion of chloroacetyl chloride (0.500 mL, 6.278 mmol) was added dropwise. The mixture was stirred for 1 h, and then the mixture was adjusted to pH>13 with 50% aq. NaOH (ca. 20 mL). The mixture was stirred and warmed to room temperature overnight, and then extracted with DCM (250 mL). The organic phase was washed with 1 N aq. HCl, followed by water. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give (5S)-5-methyl-4-(phenylmethyl)-3-morpholinone (12.74 g, 97%) as a colorless oil. LCMS: (M+H)+: 206.1.

Provenance & Evidence