Reaction Steps
The product from Example 9 (157 mg) in THF (10 ml) was treated with a 1.0 M solution of tBuOK (1.0 ml) at 0° C. and then treated with iodomethane (0.1 ml). After stirring at room temperature for 2 hours, the mixture was poured into a solution of saturated NH4Cl (15 mL) and stirred briefly before MTBE (15 mL) was added. After stirring for 5 minutes, the organic layer was separated, washed with brine, dried over Na2SO4 and concentrated to dryness. The residue was purified by column chromatography to give the title compound (134 mg). Anal. calcd for C23H25NO2: C, 79.51; H, 7.25 and N, 4.03; Found: C, 79.26; H, 7.12 and N, 3.80; 1H NMR [(CD3)2SO] δ1.16 (3H, s) 1.17 (3H, s), 2.18 (3H, s), 2.22 (1H, m), 2.46 (1H, m), 3.85 (3H, s), 5.01 (2H, m), 5.44 (1H, br s), 5.77 (1H, dd), 5.82 (1H, M), 6.10 (1H, br s), 6.52 (1H, d), 6.60 (1H, d), 6.70 (1H, d), 7.06 (1H, t) and 7.96 (1H, d); 13CNMR [(CD3)2SO] δ23.8, 28.8, 28.9, 36.5, 49.7, 55.6, 73.4, 105.6, 110.5, 113.4, 113.4, 116.1, 116.4, 127.3, 117.3, 127.3, 127.7, 132.2,133.8, 134.5, 145.8, 151.1, 156.4; APCI-MS: m/z 348 (M+H)+.
