HCID 70558534, compound → HCID 70556450, compound
Reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@:9]12[CH2:16][O:15][C@H:14]([CH2:17][O:18][C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C@H:13]1[CH2:12][O:11][NH:10]2>C(O)(=O)C.[Zn]>[NH2:10][C@@:9]1([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=2[F:1])[CH2:16][O:15][C@H:14]([CH2:17][O:18][C:19]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C@H:13]1[CH2:12][OH:11]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Zinc powder (20.0 g) was added to a solution containing (3aR,4S,6aS)-6a-(2,3-difluorophenyl)-4-((trityloxy)methyl)hexahydrofuro[3,4-c]isoxazole, obtained in Preparation Example 1-(2), (15.51 g) in acetic acid (120 mL) at 0° C. The reaction solution was allowed to warm to RT and stirred for 18 h. The insoluble matter was separated by filtration through Celite®, washing with acetic acid (100 mL) and AcOEt (300 mL), and the filtrate was concentrated. Saturated aqueous NaHCO3 solution was added carefully to neutralize the residue, and the mixture was extracted with EtOAc (3×200 mL). The combined organic layers were dried over MgSO4 and evaporated to obtain the title compound (15.42 g). 1H-NMR (400 MHz, CDCl3) δ (ppm): 2.60-2.68 (m, 1H), 2.85 (br s, 3H), 3.29 (d, J=4.8 Hz, 2H), 3.66 (dd, J=12.1, 4.8 Hz, 1H), 3.89-3.99 (m, 2H), 4.31 (d, J=9.1 Hz, 1H), 4.34-4.40 (m, 1H), 7.04-7.19 (m, 2H), 7.20-7.33 (m, 10H), 7.39-7.50 (m, 6H)