Reaction Steps
To a solution of HJC-1-79 (120 mg, 0.3 mmol) in 4 mL of MeOH was added 4 mL of saturated NH4Cl (aq.). Zinc dust (195 mg, 3.0 mmol) was added into the solution at 0° C. The reaction was stirred at 0° C. for 0.5 h. TLC indicated that the starting material was gone. The mixture was partitioned between EtOAc (50 mL) and H2O (10 mL). The organic layer was separated and washed with brine (10 mL), dried over anhydrous Na2SO4, filtered and concentrated to give an oil residue. This residue was purified with silica gel column (Hexane/EtOAc=1/1) to obtain HJC-1-86 (70 mg, 63%) as a pale brown oil. 1H NMR (600 MHz, CDCl3) δ 7.43 (d, 2H, J=8.4 Hz), 7.37 (d, 1H, J=8.4 Hz), 7.32 (d, 2H, J=8.4 Hz), 7.24 (d, 1H, J=8.4 Hz), 6.96 (s, 1H), 6.68 (d, 1H, J=8.4 Hz), 6.49 (s, 1H), 4.29 (t, 1H, J=6.6 Hz), 3.34-3.40 (m, 2H), 3.25-3.30 (m, 2H), 3.06-3.10 (m, 1H), 3.00-3.05 (m, 1H), 1.35 (d, 3H, J=6.6 Hz), 1.32 (d, 3H, J=6.6 Hz), 1.28 (t, 3H, J=6.6 Hz). 13C NMR (150 MHz, CDCl3) δ 141.1, 140.2, 139.0, 130.8, 130.5, 128.5, 128.2, 124.2, 113.2, 111.2, 106.0, 102.7, 53.6, 50.5, 40.5, 19.2, 16.9, 16.6.
