Reaction Steps
A solution of 214 (330 mg, 0.82 mmol) in THF (6 mL) and EtOH (6 mL) was treated with 10% Pd/C (33 mg) and stirred under an atmosphere of hydrogen. The reaction was monitored by TLC. Upon completion, the resultant suspension was filtered through celite, washed with ethyl acetate and then evaporated under reduced pressure. Purification (personal flashmaster: 20 g, hex:EtOAc; 2:1) afforded the title compound (118 mg, 46%) as a pale yellow solid. mp=100-105° C. 1H NMR (270 MHz; CDCl3) 1.12 (3H, d, J=6.7 Hz, CH3CH), 2.49 (1H, dd, J=16.1, 5.8 Hz, CHH), 2.89 (1H, dd, J=16.1, 4.8 Hz, CHH), 3.01-3.12 (1H, m, CHCH3), 3.48-3.74 (4H, m, 2×CH2), 3.78 (3H, s, OCH3), 3.79 (3H, s, OCH3), 5.42 (1H, s, OH), 6.42 (1H, s, CH), 6.63 (1H, s, CH), 6.77-6.81 (1H, m, CH), 6.93-6.96 (2H, m, 2×CH), 7.21 (1H, d, J=8.2 Hz, CH). 13C NMR (67.5 MHz; CDCl3) 15.39 (CH3), 34.68 (CH2), 51.43 (CH2), 52.30 (CH), 55.31 (OCH3), 55.99 (OCH3), 57.07 (CH2), 108.73 (CH), 112.54 (CH), 114.35 (CH), 114.54 (CH), 121.36 (CH), 125.48 (C), 126.56 (C), 129.29 (CH), 141.20 (C), 144.04 (C), 144.92 (C), 159.75 (C). LC/MS (ES+) tr=2.43 min, m/z 314.18 (M++H). HRMS (ES+) calcd. for C19H24NO3 314.1751, found 314.1748.
