4-Methylmorpholine → tert-Butyl [(2S)-1-(benzyloxy)-3-hydroxypropan-2-yl]carbamate

Participants

Reaction Conditions

Reaction Steps

N-BOC-O-benzylserine (5.0 g, 16.9 mmol) in 30 mL dimethoxyethane was treated with 4-methylmorpholine (2.0 mL, 18.6 mmol) and cooled to 0° C. The solution was treated with isobutylchloroformate (2.3 mL, 17.8 mmol) and the resulting suspension stirred for 15 minutes, then filtered. The solids collected were washed with 2 portions of dimethoxyethane and the washings combined with the original filtrate. This material was cooled in an ice bath and treated with a cold solution of sodium borohydride (1.93 g, 50.8 mmol) in 40 mL 1/2 saturated sodium bicarbonate and the reaction stirred for 2 hours. The mixture was diluted with water and extracted with 3 portions of ethyl acetate. The combined organic extracts were washed with saturated aqueous sodium bicarbonate, water and brine, dried, filtered and concentrated to provide the title compound. MS (DCI, NH3): 282 (MH+); 299 (M+NH4)+.

Provenance & Evidence