反应详情

温度

40 °C

To a round bottomed flask was added trans-4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexylamine (80 mg) and dichloroethane (7 ml), and the reaction mixture heated to 40° C.,. To the stirred solution was added triethylamine (100 μl), a solution of 3-nitrobenzoyl chloride (101 mg) in tetrahydrofuran/dichloromethane (6 ml, 1:1 v/v) and 4-dimethylamino pyridine (catalytic). The reaction mixture was heated at 40° C. for 24 hr, and then room temperature for 24 hr. The reaction mixture was diluted with dichloromethane (20 ml) and aqueous sodium hydroxide (16 ml, 0.5M) was added. After stirring for 0.2 hr, the layers were separated and the aqueous layer extracted with dichloromethane (2×10 ml). The combined organic phases were washed with saturated sodium hydrogen carbonate solution (15 ml) and brine (16 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. Purification via flash chromatography (SiO2, ethyl acetate/petroleum ether, gradient elution using 1:10, 1:8, 1:5, then 1:4, v/v) furnished the title compound (52 mg, 49%) as a colourless gum. δH (CDCl3): 0.18 (6H, s), 0.24 (6H, s), 0.97 (9H, s), 1.03 (9H, s), 1.34-1.61 (4H, m), 1.87-1.96 (2H, m), 2.17-2.27 (2H, m), 2.88 (1H, tt), 4.01-4.13 (1H, m), 6.08 (1H, d), 6.29 (1H, d), 6.43 (1H, dd), 6.97 (1H, d), 7.65 (1H, t), 8.18 (1H, d), 8.35 (1H, d), 8.57 (1H, s).

1. temperatureThe reaction mixture was heated at 40° C. for 24 hr
2. additionwas added
3. customthe layers were separated
4. extractionthe aqueous layer extracted with dichloromethane (2×10 ml)
5. washThe combined organic phases were washed with saturated sodium hydrogen carbonate solution (15 ml) and brine (16 ml)
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customPurification via flash chromatography (
10. washSiO2, ethyl acetate/petroleum ether, gradient elution