反应详情

1,3-Dibromo-2-propanol (1.70 ml, 16.5 mmol) and sodium carbonate (15.9 g, 150 mmol) were added to an ethanol (300 ml) solution of tert-butyl(trans-4-aminocyclohexyl)carbamate (3.21 g, 15.0 mmol) and the resulting mixture was stirred under heating to reflux overnight. After cooling, insoluble matter was removed by filtration through celite and then the filtrate was concentrated under reduced pressure. The residue was diluted with water, followed by extraction with ethyl acetate. Then the organic layer was washed with brine. The organic layer was dried over anhydrous sodium sulfate and then the solvent was evaporated under reduced pressure. The residue was dissolved in N,N-dimethylformamide (15 ml) and imidazole (2.45 g, 36.0 mmol) and tert-butyldiphenylchlorosilane (4.29 ml, 16.5 mmol) were added under ice cooling. After stirring at room temperature for 1 hour, the reaction mixture was diluted with ethyl acetate and washed with water and brine in that order. The organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography [chloroform:methanol=10:0→10:1 (v/v)] to give 2.45 g (32%) of the title compound as a colorless solid.

1. temperatureunder heating
2. temperatureto reflux overnight
3. temperatureAfter cooling
4. custominsoluble matter was removed by filtration through celite
5. concentrationthe filtrate was concentrated under reduced pressure
6. additionThe residue was diluted with water
7. extractionfollowed by extraction with ethyl acetate
8. washThen the organic layer was washed with brine
9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
10. customthe solvent was evaporated under reduced pressure
11. dissolutionThe residue was dissolved in N,N-dimethylformamide (15 ml)
12. stirringAfter stirring at room temperature for 1 hour
13. washwashed with water and brine in that order
14. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
15. customthe solvent was evaporated under reduced pressure
16. customthe residue was purified by silica gel column chromatography [chloroform:methanol=10:0→10:1 (v/v)]