反应详情

温度

50 °C

To 10 g (40.1 mmol) trans-4-Hydroxy-cyclohexylcarbamic acid benzyl ester in 40 ml DMF, 4.09 g (60.1 mmol, 1.5 eq) imidazole and 6.65 g (44.1 mmol, 1.1 eq) TBDMSCl in 20 ml DMF were added at 0° C. The mixture was warmed to 50° C. and stirred at that temperature for 2 h. A saturated solution of NaHCO3 was added, the mixture was concentrated and redissolved in ether/water. The phases were separated and the inorganic phase was extracted with ether. The combined organic phases were washed with brine, dried over Na2SO4 and concentrated. The crude product was purified on silica gel with hexane:EtOAc 5:1 as eluent yielding 11.8 g (81%) trans-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-carbamic acid benzyl ester as colorless gum, MS: 348 (M−CH3).

1. concentrationthe mixture was concentrated
2. dissolutionredissolved in ether/water
3. customThe phases were separated
4. extractionthe inorganic phase was extracted with ether
5. washThe combined organic phases were washed with brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated
8. customThe crude product was purified on silica gel with hexane:EtOAc 5:1 as eluent