O=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C@@H:6]2[CH2:13][N:14]([C:16](OC(C)(C)C)=O)[CH2:15][C@H:5]2[CH2:4][NH:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH3:16][N:14]1[CH2:15][C@@H:5]2[C@H:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[CH2:2][NH:3][CH2:4]2)[CH2:13]1To a solution of Example 71A (2.62 g, 8.66 mmol) in tetrahydrofuran (87 mL) was added lithium aluminum hydride in tetrahydrofuran (13.00 mL, 26.0 mmol) in small portions, and the mixture was stirred at room temperature for 24 hours. Water was added carefully and the product was extracted once with dichloromethane, dried over Na2SO4 and concentrated to afford the title compound. 1H NMR (500 MHz, pyridine-d5) δ ppm 7.31 (d, J=7.4, 1H), 7.20-7.17 (m, 2H), 7.13 (d, J=7.7, 1H), 4.58 (dd, J=14.5, 48.4, 2H), 4.01-3.90 (m, 2H), 3.71-3.57 (m, 2H), 3.40 (t, J=10.4, 1H), 3.19-3.05 (m, 2H), 2.71 (s, 3H), 2.66-2.52 (m, 1H); MS (ESI+) m/z 203.0 [M+H]+.
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