反应详情

To a round bottomed flask was added trans-N-[4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexyl]-3-nitrobenzamide (52 mg), dichloroethane (9 ml), water (3 ml), and trifluoroacetic acid (3 ml). The reaction mixture was heated under reflux for 15 hr, cooled to room temperature, and toluene (15 ml) was added. The reaction mixture was concentrated in vacuo, methanol (15 ml) was added, and further concentrated to remove residual trifluoroacetic acid. Purification via flash chromatography (SiO2, ethyl acetate/petroleum ether, gradient elution using 1:3, then 1:1, v/v) furnished the title compound (20 mg, 63%) as a white solid. δH ((CD3)2CO): 1.52-1.68 (4H, m), 1.87-1.95 (2H, m), 2.09-2.17 (2H, m), 2.87 (1 H, tt), 3.97-4.08 (1 H, m), 6.30 (1 H, dd), 6.38 (1 H, d), 6.99 (1 H, d), 7.77 (1H, t), 7.90 (1H, s), 7.96 (1 H, d), 8.05 (1 H, s), 8.33 (1 H, dd), 8.37 (1 H, dd), 8.68 (1 H, t); m/z (ES+) 357 )M+H)+.

1. temperatureThe reaction mixture was heated
2. temperatureunder reflux for 15 hr
3. concentrationThe reaction mixture was concentrated in vacuo, methanol (15 ml)
4. additionwas added
5. concentrationfurther concentrated
6. customto remove residual trifluoroacetic acid
7. customPurification via flash chromatography (
8. washSiO2, ethyl acetate/petroleum ether, gradient elution