反应详情

温度

80 °C

To a solution of Example 1C (1 g, 3.15 mmol) in tetrahydrofuran (10 mL) was added borane (1 M/tetrahydrofuran, 12.6 mL, 12.6 mmol). The solution was heated to 80° C. for 4 hours. Methanol (20 mL) was added, and the reaction heated at 80° C. for 1 hour. The reaction was cooled to room temperature and 1 M HCl (30 mL) was added. This solution was stirred for 30 minutes, before the solution was neutralized with sodium bicarbonate (aqueous). Dichloromethane was used to extract the product. The product was purified via flash chromatography (20-70% ethyl acetate/hexanes) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 6.77 (d, J=7.54 Hz, 1 H), 6.64-6.73 (m, 1 H), 6.48-6.59 (m, 2 H), 5.27 (s, 1 H), 3.54-3.67 (m, 1 H), 3.35-3.50 (m, 2 H), 3.20-3.29 (m, 1 H), 2.96-3.19 (m, 4 H), 2.85-2.96 (m, 1 H), 1.76-1.92 (m, 1 H), 1.59-1.75 (m, 1 H), 1.41 (s, 9 H); MS (APCI+) m/z 304.3 (M+H)+.

1. temperaturethe reaction heated at 80° C. for 1 hour
2. temperatureThe reaction was cooled to room temperature
3. extractionto extract the product
4. customThe product was purified via flash chromatography (20-70% ethyl acetate/hexanes)