Hydrochloric Acid → (R)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate

Participants

Reaction Conditions

Reaction Steps

A suspension of NaBH4 (2.71 g, 71.5 mmol) in THF (50 mL) was cooled to 0° C., treated dropwise with a solution of EXAMPLE 21A (16.21 g, 65.0 mmol) in THF (50 mL), allowed to warm to room temperature, and stirred for 2 hours. The resulting mixture was treated with concentrated HCl (13.1 mL) and ethanol (13.1 mL), heated to reflux for 12 hours, allowed to cool to room temperature, poured into brine (100 mL) and the layers were separated. The aqueous phase was extracted with ethyl acetate and the combined organic layers were washed with water and brine, dried (MgSO4), filtered, and concentrated. The concentrate was triturated with diethyl ether (50 mL) for 2 hours, cooled overnight, and the solid collected by filtration to provide the desired product (7.81 g, 51%).

Provenance & Evidence