Benzyl Alcohol → Benzyl [(4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]methylcarbamate

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-yl)acetic acid (10.0 g, 57.41 mmol), triethylamine (10 mL, 68.89 mmol) and diphenylphosphoryl azide (14 mL, 63.15 mmol) in dry toluene (100 mL) was heated and stirred at 85° C. When the gas evolution had ceased stirring was continued for an additional hour. Dry benzyl alcohol (6.3 mL, 63.15 mmol) was added and heating was continued for 17 hours. After evaporation in vacuo, the residue was partitioned between dichloromethane, water and brine. The aqueous phase was further extracted twice with dichloromethane. The combined organic phases were washed twice with saturated sodium hydrogen carbonate. After drying (magnesium sulphate), filtration, and concentration in vacuo of the organic phase, the residue was subjected to flash column chromatography with dichloromethane as eluent. This afforded 6.4 g (40%) of (R)-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylmethyl)carbamic acid benzyl ester as an oil.

Provenance & Evidence