反应详情

cis-N-Benzyl-N-[4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexyl] amine (0.084 g) was dissolved in dichloroethane (7 ml), and triethylamine (0.045 ml) and 4-dimethylaminopyridine (catalytic) added. Propionyl chloride (0.028 ml) was then added, and the mixture stirred at room temperature for 60 hr. The reaction mixture was partitioned between dichloromethane (10 ml) and saturated aqueous sodium hydrogen carbonate (10 ml). The aqueous layer was extracted with dichloromethane (2×10 ml) and the combined organic extracts washed with brine (10 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was dissolved with stirring in dichloroethane (16 ml) and heated with a mixture of water (10 ml), methanol (5 ml) and trifluoroacetic acid (10 ml) at 80° C. for 17 hr. Toluene (25 ml) was then added and the mixture concentrated in vacuo. Methanol (25 ml) was then added and the mixture again concentrated in vacuo. Purification via flash chromatography (SiO2, ethyl acetate/petroleum ether) afforded the title compound (0.021 g, 37%) as a colourless solid. Rf 0.20 (ethyl acetate/petroleum ether, 1:1, v/v); m/s(ES+) 354.17 (M+H)+.

1. customThe reaction mixture was partitioned between dichloromethane (10 ml) and saturated aqueous sodium hydrogen carbonate (10 ml)
2. extractionThe aqueous layer was extracted with dichloromethane (2×10 ml)
3. washthe combined organic extracts washed with brine (10 ml)
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. dissolutionThe residue was dissolved
8. stirringwith stirring in dichloroethane (16 ml)
9. temperatureheated with a mixture of water (10 ml), methanol (5 ml) and trifluoroacetic acid (10 ml) at 80° C. for 17 hr
10. additionToluene (25 ml) was then added
11. concentrationthe mixture concentrated in vacuo
12. additionMethanol (25 ml) was then added
13. concentrationthe mixture again concentrated in vacuo
14. customPurification via flash chromatography (SiO2, ethyl acetate/petroleum ether)