반응 #53938

반응 방정식

AcOH

Methyl-(4-oxo-cyclohexyl)-carbamic acid tert-butyl ester

(4-Carboxy-butyl)-triphenyl-phosphonium bromide

NaH

→

5-[4-(tert-Butoxycarbonyl-methyl-amino)-cyclohexylidene]-pentanoic acid

수율 85.6%

용매

DMF

DMF

반응 조건

후처리

1. 1
   workup.ADDITIONthe slurry was diluted
2. 2
   기타the solvent was evaporated under reduced pressure
3. 3
   workup.DISSOLUTIONThe residue was dissolved in ether
4. 4
   추출water, and the inorganic layer was extracted with ether
5. 5
   기타The combined organic phases were dried over and the crude materil
6. 6
   기타was purified by column chromatography with ETOAc/hexane

실험 절차

5 g (21.99 mmol) Methyl-(4-oxo-cyclohexyl)-carbamic acid tert-butyl ester and 12.68 g (28.59 mmol) (4-Carboxy-butyl)-triphenyl-phosphonium bromide were dispended in 50 ml DMF. In small portions 2.49 g (57.2 mmol, 55%) NaH were added and the slurry was diluted by adding 50 ml DMF. The mixture was stirred at RT over night, 10 ml AcOH were added and the solvent was evaporated under reduced pressure. The residue was dissolved in ether and water, and the inorganic layer was extracted with ether. The combined organic phases were dried over and the crude materil was purified by column chromatography with ETOAc/hexane to give 5.86 g (83%)5-[4-(tert-Butoxycarbonyl-methyl-amino)-cyclohexylidene]-pentanoic acid.

출처