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To a solution of 19 (400 mg, 0.82 mmol) in THF (20 mL) at 0° C. was added LiAlH4 (48 mg, 1.2 mmol) in several portions. The reaction mixture was allowed to stir at 0° C. for an additional 10 min then quenched with H2O (25 μL). The solvent was removed by rotary evaporation, and the crude product was purified by flash column chromatography (EtOAc:hexanes, 2:1-4:1) to give 20 (280 mg, 0.66 mmol, 80%) as a colorless oil: 1H NMR (500 MHz, CDCl3) δ 2.12 (s, 6H), 2.39 (s, 3H), 2.64-2.67 (dd, J=2.0, 12.0 Hz, 1H), 2.70-2.90 (m, 2H), 2.98-3.03 (dd, J=5.5, 12.5, Hz, 1H), 3.40-3.44 (dd, J=3.0, 11.5 Hz, 1H), 3.56-3.58 (dd, J=3.0, 6.0 Hz, 1H), 3.65-3.69 (dd, J=7.5, 11.5 Hz, 1H), 3.76-3.79 (d, J=13.0 Hz, 1H), 3.83-3.86 (d, J=13.0 Hz, 1H), 3.90-3.94 (dd, J=5.0, 12.5 Hz, 1H), 3.99-4.03 (dd, J=5.5, 12.5 Hz, 1H), 5.15-5.17 (dd, J=1.0, 10.5 Hz, 1H), 5.23-5.27 (dd, J=1.0, 18.5 Hz, 1H), 5.80-5.96 (m, 3H), 6.86 (s, 1H), 6.99 (s, 1H), 7.24-7.40 (m, 5H); 13C NMR (125 MHz, CDCl3) δ 13.5, 21.2, 37.7, 46.4, 49.5, 54.0, 60.8, 70.9, 79.4, 98, 9, 106.9, 117.2, 120.4, 123.7, 127.6, 128.6, 128.7, 128.9, 135.0, 139.2, 149.8, 151.8, 160.6; LCQ-MS (M+H+) calcd for C27H36N3O2 434. found 434; LC-TOF-MS (M+H+) calcd for C27H36N3O2 434.28075. found 434.28071.

1. customthen quenched with H2O (25 μL)
2. customThe solvent was removed by rotary evaporation
3. customthe crude product was purified by flash column chromatography (EtOAc:hexanes, 2:1-4:1)