Reaction Steps
A mixture of the product from Example 28B (0.53 g, 0.93 mmol) and 10% Pd/C (0.053 g, 0.047 mmol) in methanol (50 mL) and conc. HCl (86 μL, 1.02 mmol) was hydrogenated under 60 psi of hydrogen gas at ambient temperature for 1 h. The resulting mixture was filtered and concentrated to obtain title compound (0.47 g, quantitative yield). 1H NMR (DMSO-d6) δ: 1.28 (s, 9H), 1.84 (m, 1H), 2.46 (m, 1H), 2.85 (m, 1H), 2.94 (m, 1H), 4.65 (dd, 2H), 5.18 (q, 1H), 6.96 (d, 1H), 7.26 (s, 2H), 7.31 (s, 1H), 7.51 (t, 1H), 7.69 (d, 1H), 7.91 (d, 1H), 8.02 (br s, 2H), 8.59 (s, 1H), 9.19 (s, 1H). 1H NMR (methanol-d4) δ: 1.32 (s, 9H), 1.91 (m, 1H), 2.59 (m, 1H), 2.90 (m, 1H), 3.00 (m, 1H), 3.45 (dd, 2H), 4.71 (dd, 21H), 5.30 (t, 1H), 7.28 (s, 2H), 7.32 (s, 1H), 7.57 (t, 1H), 7.67 (d, 1H), 7.90 (d, 1H), 8.48 (s, 1H). MS (ESI) m/z: 436.2 [M+H]+ Anal Calcd for C24H29N5O3.HCl.1.8 H2O: C, 57.15; H, 6.71; N, 13.88. Found: C, 57.21; H, 6.55; N, 13.60.
