Reaction Steps
To a solution of 10 (300 mg, 0.70 mmol) in THF (15 mL) at 0° C. was added LiAlH4 (55 mg, 1.4 mmol) in several portions. The reaction mixture was allowed to stir at 0° C. for 20 min then carefully quenched with H2O (50 μL). The solvent was removed by rotary evaporation, and the crude product was purified by flash column chromatography (EtOAc/hexanes, 1:2-1:1) to give 11 (205 mg, 0.60 mmol, 86%) as a colorless oil: 1H NMR (500 MHz, CDCl3) δ 2.10 (s, 6H), 2.30-2.38 (br s, 1H), 2.39 (s, 3H), 2.83-2.88 (dd, J=4.0, 13.5 Hz, 1H), 2.90-2.94 (dd, J=5.5, 14.0 Hz, 1H), 3.40-3.57 (m, 3H), 3.62-3.67 (m, 2H), 3.74-3.78 (dd, J=5.0, 11.5 Hz, 1H), 4.00-4.04 (dd, J=6.0, 12.5 Hz, 1H), 4.10-4.15 (dd, J=5.0, 13.5 Hz, 1H), 5.15-5.18 (dd, J=1.5, 11.5 Hz, 1H), 5.24-5.28 (dd, J=1.5, 17.5 Hz, 1H), 6.88 (s, 1H), 7.05 (s, 1H); 13C NMR (125 MHz, CDCl3) δ 13.3, 14.4, 21.2, 21.3, 36.0, 43.0, 60.6, 61.8, 61.9, 71.5, 77.1, 77.3, 77.6, 81.5, 106.9, 117.4, 120.9, 124.0, 128.7, 135.0, 150.5, 151.7, 160.3, 171.4; LCQ-MS (M+H+) calcd for C20H29N2O3 345. found 345; LC-TOF-MS (M+H+) calcd for C20H29N2O3 345.21782. found 345.21772.
