Tetrahydrofuran → (S)-4-(pyridin-2-yl)oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-2-amino-2-(pyridin-2-yl)ethanol bis hydrochloride (0.80 g, 5.8 mmol) in water (50 mL) cooled to 0° C. was added potassium hydroxide (2.6 g, 46 mmol) and the reaction stirred at 0° C. for 15 minutes, followed by the addition of THF (100 mL) and the reaction cooled to 0° C. To the reaction was next added bis(trichloromethyl) carbonate (1.7 g, 5.8 mmol) and the reaction stirred at 0° C. for 2 hours. The reaction was diluted with EtOAc (300 mL) and the layers were separated. The organic layer was washed with water (100 mL) and brine (100 mL), dried over MgSO4 and concentrated in vacuo. The crude material was chromatographed using EtOAc as eluent to yield (S)-4-(pyridin-2-yl)oxazolidin-2-one (0.20 g, 21%).

Provenance & Evidence