Reaction Steps
To a solution of compound 15 (1.13 g, 3 mmol) in EtOH (30 mL) was added Ra—Ni (0.20 g, 10% wet basis) and the mixture was subjected to hydrogenation in Parr apparatus at 20 psi for 6 hours. After filtering over the pad of celite, the solution was concentrated and purified over silica column, eluting with CH2Cl2:MeOH (95:5) and then changing to (92:8) afforded compound 16 as a light yellow thick oil (0.85 g, 82%). IR (KBr) νmax. cm−1: 3441, 3421 (NH), 3042 (Ar—H), 2960 (Alph-H), 1699, 1696 (C═O), 1607, 1577 (C═C), 1240 (C—N), 1165 (C—O). 1H NMR (500 MHz, CDCl3) δ=1.48 (s, 9H, (C(CH3)3), 2.16 (s, 3H, CH3), 3.38 (br. s, 4H, 2CH2), 3.52 (br. s, 4H, 2CH2), 5.28 (br. s, 2H, NH2), 5.49 (s, 2H, CH2), 6.78 (dd, 1H, J=2.3, 9.3 Hz, H-6), 6.80 (br. s, 1H, H-2), 6.87 (d, 1H, J=9.2 Hz, H-5). 13C NMR (125.7 MHz, CDCl3) δ=20.97 (CH3), 28.35 (C(CH3)3), 42.53 (CH2), 46.26 (CH2), 62.54 (CH2), 79.85 (C(CH3)3), 112.10 (aromatic-C), 112.38 (aromatic-C), 117.09 (aromatic-C), 130.22 (aromatic-C), 135.03 (aromatic-C), 143.02 (aromatic-C), 154.58 (CO), 170.51 (CO). Calculated (%) for C18H28N4O3 (348.22); C, 62.05; H, 8.10; N, 16.08. found (%); C, 62.00; H, 8.15; N, 16.00.
