反应详情

To a solution of 2-chloro-5-nitropyridine (500 mg, 3.1 mmol) in THF (30 mL) was added tert-butyl piperidin-3-ylcarbamate (700 mg, 3.5 mmol) and triethylamine (0.64 mL, 4.6 mmol) and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated to dryness, the residue was dissolved in dichloromethane and washed with 1 N HCl aq. and water. The organic layer was dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated to dryness. The residue was dissolved in tetrahydrofuran (30 mL), degassed with nitrogen, charged with catalytic 10 wt. % Pd/C (0.3 g) and the reaction mixture was placed under an atmosphere of hydrogen (40 Psi) until the reduction was complete as indicated by LCMS analysis. The reaction mixture was filtered over diatomaceous earth and the filtrate was concentrated to provide the desired product (850 mg, 93%) as a purple solid: ESI MS m/z 293 [C15H24N4O2+H]+.

1. concentrationThe reaction mixture was concentrated to dryness
2. dissolutionthe residue was dissolved in dichloromethane
3. washwashed with 1 N HCl aq. and water
4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationthe filtrate was concentrated to dryness
7. dissolutionThe residue was dissolved in tetrahydrofuran (30 mL)
8. customdegassed with nitrogen
9. additioncharged with catalytic 10 wt. % Pd/C (0.3 g)
10. filtrationThe reaction mixture was filtered over diatomaceous earth
11. concentrationthe filtrate was concentrated