Dimethyl Sulfoxide → HCID 71226801, compound

Temperature

0 °C

To a round bottom flask was added 2-(4-nitrophenyl)-2-azabicyclo[2.2.1]heptan-6-ol (150 mg, 0.640 mmol), Et3N (0.446 mL, 3.20 mmol) and CH2Cl2 (3 mL). The reaction was cooled to 0° C. Pyridine sulfur trioxide (510 mg, 3.20 mmol) and DMSO (0.909 mL, 12.81 mmol) were mixed in a vial until the solution turned clear and then this clear solution was added to the reaction mixture at 0° C. The reaction was slowly warmed to rt and stirred at rt for 2 hrs. The reaction was diluted with CH2Cl2 (25 ml). The organic solution was washed with water (2×20 ml) and saturated aqueous NaCl (20 ml). The organic layer was dried with MgSO4, filtered and concentrated. The resulting residue was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-100% EtOAc/Hex to give the product, 2-(4-nitrophenyl)-2-azabicyclo[2.2.1]heptan-6-one, (80 mg, 0.344 mmol, 54% yield) as a yellow solid. Anal. Calcd. for C12H12N2O3 m/z 232.2, found: 233.2 (M+H)+.

1. additionthis clear solution was added to the reaction mixture at 0° C
2. temperatureThe reaction was slowly warmed to rt
3. washThe organic solution was washed with water (2×20 ml) and saturated aqueous NaCl (20 ml)
4. dry with materialThe organic layer was dried with MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe resulting residue was purified
8. washeluting with a gradient of 0-100% EtOAc/Hex

ORD record

ord-032e3fc748bc43b4b7c98729e8771593

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08710049B2