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温度

0 °C

Into a Parr bottle was added 10% palladium-on-carbon (50% wet, 1487.2 mg) followed by ethanol (10 mL) which was previously bubbled with nitrogen and cooled to 0° C. with an ice-water bath. (R)-(1-(6-Amino-5-nitropyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (10.612 g, 33.228 mmol) in ethanol (84 mL) was added into the Parr bottle followed by concentrated hydrochloric acid (8.59 mL, 99.6 mmol) dissolved in ethanol (10 mL) under a nitrogen atmosphere. The reaction mixture was purged with nitrogen and evacuated 3 times. The mixture was submitted to a hydrogen atmosphere (45 PSI). A drop in pressure was observed and it was increased to 46 PSI. This process was repeated several times over a period of 30 minutes. The reaction mixture was shaken for a total of 1 h. Then it was filtered through Celite and the residue was rinsed with ethanol (1 L). The solvent was removed under reduced pressure and the residue was redissolved in methanol. The solvent was removed under reduced pressure and the solid was dried under high vacuum to afford the title compound (12.0 g). The material was used without further purification. 1H NMR (400 MHz, CD3OD) δ 1.67-1.81 (m, 2H) 1.83-2.10 (m, 6H) 2.85-2.95 (m, 1H) 3.32-3.55 (m, 5H) 3.66 (dt, 1H) 3.89 (d, 1H) 3.97 (dd, 1H) 6.38 (d, 1H) 7.64 (d, 1H); MS (ES+) (M+H) 290.2.

1. customwas previously bubbled with nitrogen
2. customThe reaction mixture was purged with nitrogen
3. customevacuated 3 times
4. temperatureit was increased to 46 PSI
5. customof 30 minutes
6. filtrationThen it was filtered through Celite
7. washthe residue was rinsed with ethanol (1 L)
8. customThe solvent was removed under reduced pressure
9. dissolutionthe residue was redissolved in methanol
10. customThe solvent was removed under reduced pressure
11. customthe solid was dried under high vacuum