Trifluoroacetic acid → HCID 117702518, compound

To a solution of tert-butyl 5-(pyridin-2-ylethynyl)bicyclo[3.2.1]octan-1-ylcarbamate (1.1 g, 3.37 mmol) in DCM (5.0 mL) was added 2,2,2-trifluoroacetic acid (2.0 mL). After stirring at room temperature for two hours, the reaction mixture was concentrated under reduced pressure. The residue was diluted with water (10 mL) and extracted with ethyl ether (10 mL) to remove non-amine organic impurity. The aqueous layer was basified with NaOH to pH=12 and then extracted with DCM (3×10 mL). The combined DCM layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford 600 mg (78%) of the title compound, 5-(pyridin-2-ylethynyl)bicyclo[3.2.1]oct-1-ylamine. 1HNMR (500 MHz, CDCl3): δ 8.51 (d, J=5.0 Hz, 1H), 7.59-7.56 (m, 1H), 7.35 (d, J=7.5 Hz, 1H), 7.16-7.13 (dd, J=7.0, 5.0 Hz, 1H), 2.42 (s, 2H), 2.15-1.54 (m, 12H); ESI-MS m/z: 227 (M+H)+.

1. concentrationthe reaction mixture was concentrated under reduced pressure
2. additionThe residue was diluted with water (10 mL)
3. extractionextracted with ethyl ether (10 mL)
4. customto remove non-amine organic impurity
5. extractionextracted with DCM (3×10 mL)
6. washThe combined DCM layer was washed with brine
7. dry with materialdried over Na2SO4
8. concentrationconcentrated under reduced pressure

ORD record

ord-df309d6f6278429895eee52dd9239615

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09212165B2