Water → HCID 71258444, compound

Sodium hydride (60 wt % dispersion in liquid paraffin, 151 mg, 3.46 mmol) in N,N-dimethylformamide (5 mL) was mixed with tert-butyl 3-hydroxyazetidine-1-carboxylate (500 mg, 2.89 mmol) in N,N-dimethylformamide (3 mL) under cooling with ice and stirred for 30 minutes, and the resulting reaction mixture was mixed with 2,2,2-trifluoroethyl trifluoromethanesulfonate (0.499 mL, 3.46 mmol) under cooling with ice and then stirred at room temperature for 5 hours. After addition of water, the reaction mixture was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1→1/1(v/v)) to give the title compound as a colorless solid (350 mg, yield 48%).

1. temperatureunder cooling with ice
2. customthe resulting reaction mixture
3. temperatureunder cooling with ice
4. stirringstirred at room temperature for 5 hours
5. extractionthe reaction mixture was extracted with ethyl acetate
6. washthe organic layer was washed with saturated aqueous sodium chloride
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1→1/1(v/v))

ORD record

ord-4136ab0f55f743ef8fdc86bfbfc2248c

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09216999B2