HCID 57827394, compound → (+/-)-[(3R*,4S*)-4-Amino-4-(2-fluorophenyl)tetrahydrofuran-3-yl]methanol

Participants

Reaction Steps

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).

Provenance & Evidence