反应详情

To a solution of 1.15 g of 1-(t-butoxycarbonyl)-4-(1-bromo-2-oxoethyl)-piperidine (from Example 292, Step C) in 15 mL ethanol was added 388 mg of 2-aminopyridine. After refluxing for 18 hours, the solvent was evaporated. The mixture was partitioned between EtOAc and saturated sodium bicarbonate solution. Aqueous layer was extracted with EtOAc (3×). The combined organic phase was washed with brine, dried over MgSO4 and concentrated. The residue was purified by flash chromatography with 50% EtOAc in hexanes, followed by 100% EtOAc to give 401 mg of the title compound as a solid. 1H NMR (500 MHz, CDCl3) δ1.48 (s, 9H), 1.70 (m, 2H), 2.06 (d, J=13 Hz, 2H), 2.93-3.02 (m, 3H), 4.26 (br, 2H), 6.87 (t, J=6.8 Hz, 1H). 7.21(m, 1H), 7.44(s, 1H), 7. 69(d, J=9.2 Hz,1H), 7.99 (d, J=6.9 Hz, 1H).

1. temperatureAfter refluxing for 18 hours
2. customthe solvent was evaporated
3. customThe mixture was partitioned between EtOAc and saturated sodium bicarbonate solution
4. extractionAqueous layer was extracted with EtOAc (3×)
5. washThe combined organic phase was washed with brine
6. dry with materialdried over MgSO4
7. concentrationconcentrated
8. customThe residue was purified by flash chromatography with 50% EtOAc in hexanes