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

Temperature

0 °C

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%).

1. temperaturethe reaction cooled to 0° C
2. stirringthe reaction stirred at 0° C. for 2 hours
3. customthe layers were separated
4. washThe organic layer was washed with water (100 mL) and brine (100 mL)
5. dry with materialdried over MgSO4
6. concentrationconcentrated in vacuo
7. customThe crude material was chromatographed

ORD record

ord-3902f1ff570e4d09a7721bbedeef7b92

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08865726B2