Reaction Steps
A solution of 14g (120 mg, 0.23 mmol) in THF (45 mL) was hydrogenated over PtO2 (30 mg) at 55 psi for 1.5 h. After removal of the catalyst the solution was concentrated to a small volume under reduced pressure below 30° C., and then diluted with petroleum ether to give 15g (140 mg. 92%), mp 109-111 (C. 1H NMR [(CD3)2SO] δ 11.41 (s, 1 H, NH), 8.07 (d, J=8.8 Hz, 1 H, H-6), 7.75 (d, J=8.2 Hz, 1 H, H-9), 7.64 (s, 1 H, H-4), 7.45 (t, J=7.5 Hz, 1 H, H-8), 7.28 (t, J=7.6 Hz, 1 H, H-7), 7.00 (d, J=1.2 Hz, 1 H, H-3'), 6.73 (d, J=1.9 Hz, 1 H, H-4' or 6'), 6.48 (d, J=2.0 Hz, 1 H, H-4'or 6'), 5.98, 5.96 (2×s, 2 H, NH2), 4.66 (dd, J=10.7, 9.0 Hz, 1 H, H-2), 4.41 (dd, J=11.0, 1.4 Hz, 1 H, H-2), 4.19 (t, J=5.7 Hz, 2 H, OCH2), 4.12-4.04 (m, 1 H, H-1), 3.96 (dd, J=10.9, 3.0 Hz, 1 H, CHHCl), 3.77 (s, 3 H, OCH3), 3.72 (dd, J=11.0, 8.2 Hz, 1 H, CHHCl), 2.73 (t, J=5.7 Hz, 2 H, OCH2CH2), 2.28 (s, 6 H, N(CH3)2).
