反应详情

温度

22 °C

To a solution of 1.25 g (4.26 mmol) of ethyl 4-(2-(tert-butoxycarbonylamino)ethyl)benzoate in 40 mL of dry THF under a nitrogen atmosphere was added dropwise, 4.7 mL (4.7 mmol) of NaHMDS (1.0 M in THF) at 0° C. After stirring for 10 min, 0.50 mL (5.3 mmol) of dimethyl sulfate was added and the reaction was warmed to 22° C. and stirred for about 16 h. The reaction was quenched by adding 25 mL of saturated NaHCO3 and the mixture was extracted with DCM (2×25 mL). The combined organic extracts were dried (Na2SO4) and evaporated and the residue was purified by flash chromatography on silica gel, eluting first with hexane and then gradually increasing to 10% ethyl acetate/hexane to give ethyl 4-(2-(tert-butoxycarbonyl(methyl)amino)ethyl)benzoate as a colorless oil.

1. customat 0° C
2. stirringstirred for about 16 h
3. customThe reaction was quenched
4. additionby adding 25 mL of saturated NaHCO3
5. extractionthe mixture was extracted with DCM (2×25 mL)
6. dry with materialThe combined organic extracts were dried (Na2SO4)
7. customevaporated
8. customthe residue was purified by flash chromatography on silica gel
9. washeluting first with hexane
10. temperaturegradually increasing to 10% ethyl acetate/hexane