反応 #53938

反応方程式

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

収率 85.6%

溶媒

DMF

DMF

反応条件

後処理

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

実験手順

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.

出典