Acetic Acid → ((2R,3R,4S*)-4-Amino-4-(2,4-difluorophenyl)-2-methyltetrahydrofuran-3-yl)methanol

反応式

Br[C:2]1[C:3]([F:18])=[CH:4][C:5]([F:17])=[C:6]([C@:8]23[CH2:15][O:14][C@H:13]([CH3:16])[C@H:12]2[CH2:11][O:10][NH:9]3)[CH:7]=1.C(O)(=O)C>C1COCC1.[Zn]>[NH2:9][C@@:8]1([C:6]2[CH:7]=[CH:2][C:3]([F:18])=[CH:4][C:5]=2[F:17])[CH2:15][O:14][C@H:13]([CH3:16])[C@H:12]1[CH2:11][OH:10]

参加物

実験手順

(3aR*,4R*,6aS*)-6a-(5-Bromo-2,4-difluorophenyl)-4-methylhexahydro furo[3,4-c]isoxazole (200 mg, 0.62 mmol) was dissolved in THF (10 mL). Zinc dust (0.49 g, 7.50 mmol) was added, followed by acetic acid (143 μl, 2.50 mmol) and the reaction was stirred at room temperature overnight. The reaction was filtered through Celite®, washing with MeOH and the filtrate was concentrated in vacuo. The residue was basified with saturated NaHCO3 and DCM added. The mixture was filtered and the layers separated. The aqueous layer was extracted with DCM (×2) and the combined organics were dried (MgSO4) and concentrated to leave the title compound (120 mg).