Reaction Steps
A mixture of 110b (1.032 g, 3 mmol) and Ra-Ni (0.24 g, wet) in 30 mL of EtOH was hydrogenated (50 psi of H2) at room temperature for 6 hr. The reaction mixture was filtered and the filtrate was evaporated. The residue was suspended in 20 mL of MeCN and the suspension was filtered to give 0.856 g (90%, 2 crops) of 113 as a white solid. Analytical sample (as white needles) was obtained by recrystallization from MeOH/MeCN. MP: 216°-221° C. (dec.). MS: (EI) m/e 317.0340 (37%, M+ =317.0334). 1H NMR (DMSO-d6): d 7.71 (s, 1, 7-H), 7.29 (s, 1, 4-H), 6.93 (br s, 2, 2-NH2), 6.23 (dd, 1, 1'-H, J1'-2' =8.5 Hz, J1'-2" =6.0 Hz), 5.40 (t, 1, 5'-OH, J5'-5'OH =4.5 Hz), 5.34 (d, 1, 3'-OH, J3'-3'OH =4.0 Hz), 4.40 (m, 1, 3'-H, J3'-2' =7.0 Hz, J3'-2" =2.0 Hz, J3'-4' =2.5 Hz), 3.82 (m, 1, 4'-H, J4'-5' =2.5 Hz), 3.68 (m, 2, 5'-H), 2.40 (m, 1, 2'-H, J2'-2" =13.0 Hz), 2.05 (m, 1, 2"-H). 13C NMR (DMSO-d6): d 155.85 (C2), 143.16 (C3a); 132.40 (C7a), 122.94, 119.77 (C5 and C6), 115.35 (C4), 110.69 (C7), 86.91 (C4'), 83.87 (C1'), 70.20 (C3'), 60.74 (C5'), 38.05 (C2'). Anal. Calcd. for C12H13Cl2N3O3 : C, 45.30; H, 4.12; N, 13.21. Found: C, 45.44; H, 4.10; N, 13.28.
