반응 #591093

반응 방정식

KHMDS

methanesulfonic acid 3-(4-bromo-2-methyl-phenyl)-4-tert-butoxycarbonylamino-butyl ester

→

3-(4-bromo-2-methyl-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

수율 95.0%

용매

THF

반응 조건

후처리

1. 1
   기타The ice-bath was removed
2. 2
   workup.ADDITIONA saturated solution of NH4Cl was added to the reaction mixture
3. 3
   추출the resulting mixture was extracted with EtOAc
4. 4
   세척The combined organic extracts were washed with water and brine
5. 5
   건조dried over MgSO4
6. 6
   여과filtered
7. 7
   기타evaporated under reduced pressure
8. 8
   기타The residue was purified via flash chromatography (hexane/EtOAc, 8/2)

실험 절차

KHMDS (0.5 M in toluene, 186 mL, 0.09303 mol) was added at 0° C. to methanesulfonic acid 3-(4-bromo-2-methyl-phenyl)-4-tert-butoxycarbonylamino-butyl ester (36.9 g, 0.08457 mol) dissolved in THF (400 mL). The ice-bath was removed and the mixture was stirred at room temperature for 2 hours. A saturated solution of NH4Cl was added to the reaction mixture and the resulting mixture was extracted with EtOAc. The combined organic extracts were washed with water and brine, dried over MgSO4, filtered, and evaporated under reduced pressure. The residue was purified via flash chromatography (hexane/EtOAc, 8/2) to give 27.3 g (95% yield) of 3-(4-bromo-2-methyl-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester as a clear oil.

출처