反应详情

Zinc (powder, 21 g) was added to a solution containing (±)-(3aS*,6aS*)-6a-(2-fluorophenyl)tetrahydrofuro[3,4-c]isoxazole (5.6 g) in acetic acid (140 mL) at RT. The reaction solution was stirred at RT for 16 h. The insoluble matter was separated by filtration through celite and the filtrate was concentrated under reduced pressure. EtOAc and a sodium bicarbonate solution were added to the residue, and the organic layer was separated. The organic layer was washed with saturated aqueous sodium chloride. The aqueous layer was further extracted with EtOAc three times. The organic layers were combined and dried over anhydrous MgSO4. The insoluble matter was separated by filtration and the filtrate was concentrated under reduced pressure to obtain the title compound (5.46 g). ESI-MS; m/z 212 [M+H]+. 1H NMR (CDCl3) δ ppm 2.81-2.88 (m, 1H), 3.83 (dd, J=6.8, 12.0 Hz, 1H), 3.92 (dd, J=3.2, 8.8 Hz, 1H), 3.94-4.00 (m, 2H), 4.07 (dd, J=8.4, 9.2 Hz, 1H), 4.14 (dd, J=1.2, 8.8 Hz, 1H), 7.09 (ddd, J=1.2, 8.0, 12.4 Hz, 1H), 7.16 (ddd, J=1.2, 7.6, 8.0 Hz, 1H), 7.26-7.32 (m, 1H), 7.53 (dt, J=2.0, 8.0 Hz, 1H).

1. customThe insoluble matter was separated by filtration through celite
2. concentrationthe filtrate was concentrated under reduced pressure
3. additionEtOAc and a sodium bicarbonate solution were added to the residue
4. customthe organic layer was separated
5. washThe organic layer was washed with saturated aqueous sodium chloride
6. extractionThe aqueous layer was further extracted with EtOAc three times
7. dry with materialdried over anhydrous MgSO4
8. customThe insoluble matter was separated by filtration
9. concentrationthe filtrate was concentrated under reduced pressure