Benzyl Bromide → HCID 54085496, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-tert-butoxycarbonyl-D-valinol (10 g, 49.3 mmol) and benzylbromide (5.86 mL, 49.3 mmol) in anhydrous dimethyl formamide (50 mL) is added at -5° C. and under nitrogen, potassium-tert-butoxide (11.06 g, 98.6 mmol) as a solid, portionwise, an in such a way that the internal temperature does not exceed +5° C. The reaction mixture is stirred for 2 hours at 0° C., diluted with ethyl acetate (2×300 mL), extracted with a 1N solution of potassium hydrogen sulfate (50 mL) and water (250 mL) and is washed twice with water (2×200 mL). After drying of the organic phase over anhydrous sodium sulfate, filtration and concentration under vacuum, the oil is purified by flash chromatography (silica gel, ethyl acetate/petroleum ether: 1/9, Rf: 0.42) to provide N-tert-butoxycarbonyl-O-benzyl-D-valinol as a colorless oil (9.95 g, 69% yield).

Provenance & Evidence