Reaction Steps
A solution of 14d (140 mg, 0.32 mmol) in THF (10 mL) was hydrogenated over PtO2 at 50 psi for 2 h. After removal of the catalyst, the solution was concentrated to a small volume below 25° C. and diluted with iPr2O to give 15d (124 mg, 95%), mp 250-255° C. 1H NMR [(CD3)2SO] δ 11.56 (d, J=1.6 Hz, 1 H, NH), 8.08 (d, J=8.4 Hz, 1 H, H-6), 7.76 (d, J=8.2 Hz, 1 H, H-9), 7.70 (s, 1 H, H-4), 7.46 (t, J=7.6 Hz, 1 H, H-8), 7.40 (d, J=8.8 Hz, 1 H, H-7'), 7.28 (t, J=7.6 Hz, 1 H, H-7), 7.16 (d, J=2.4 Hz, 1 H, H-4'), 7.08 (d, J=1.8 Hz, 1 H, H-3'), 6.91 (dd, J=8.8, 2.5 Hz, 1 H, H-6'), 5.98 (s, 2 H, NH2), 4.73 (dd, J=10.8, 8.9 Hz, 1 H, H-2), 4.51 (dd, J=10.9, 1.7 Hz, 1 H, H-2), 4.17-4.08 (m, 1 H, H-1), 3.98 (dd, J=11.0, 3.1 Hz, 1 H, CHHCl), 3.78 (s, 3 H, OCH3), 3.75 (dd, J=11.0, 8.1 Hz, 1 H, CHHCl).
