Dimethyl Sulfoxide → HCID 71227122, compound

Temperature

0 °C

To a round bottom flask was added 4-((1S,4R)-6-hydroxy-2-azabicyclo[2.2.1]heptan-2-yl)benzonitrile (329 mg, 1.535 mmol), Et3N (777 mg, 7.68 mmol) and CH2Cl2 (7.2 ml). The resulting solution was cooled to 0° C. In a separate vial, pyridine sulfur trioxide (1.22 gm, 7.68 mmol) and DMSO (2.4 gm, 30.7 mmol) were mixed until the solution turned clear. The resulting solution was then added to the reaction at 0° C. The reaction mixture was slowly warmed to rt and stirred for an additional 1 hr. After this time, the solution was diluted with CH2Cl2. The resulting solution was wash with water (2×) and saturated aqueous NaCl. The organic layer was separated, dried over 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 product 4-((1R,4S)-6-oxo-2-azabicyclo[2.2.1]heptan-2-yl)benzonitrile (281 mg, 1.324 mmol, 86% yield) as colorless oil. Anal. Calcd. for C13H12N2O m/z 212.2, found: 213.0 (M+H)+.

1. additionThe resulting solution was then added to the reaction at 0° C
2. temperatureThe reaction mixture was slowly warmed to rt
3. washThe resulting solution was wash with water (2×) and saturated aqueous NaCl
4. customThe organic layer was separated
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe resulting residue was purified
9. washeluting with a gradient of 0-100% EtOAc/Hex

ORD record

ord-cd44ce2de7f34f01816c180a35997e68

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08815909B2