Reaktion #53938

Reaktionsgleichung

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

Ausbeute 85.6%

Lösungsmittel

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle