Reaktion #63722

Reaktionsgleichung

2,5-dimethylcyclopentanol

compound 1

N-t-butoxycarbonyl-1-aminocyclopropanecarboxylic acid

→

2,5-Dimethylcyclopentyl N-t-butoxycarbonyl-1-aminocyclopropanecarboxylate

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe precipitated dicyclohexylurea was removed by filtration
2. 2
   Sonstigethe filtrate was evaporated
3. 3
   workup.ADDITIONEthyl acetate was then added to the residue
4. 4
   Filtrationthe mixture was filtered again
5. 5
   WaschenThe filtrate was washed with 1M hydrochloric acid, saturated aqeuous sodium bicarbonate, and water
6. 6
   Trocknendried over magnesium sulfate
7. 7
   Sonstigethe solvent was evaporated to a colorless oil (1.18 g. 83%)
8. 8
   SonstigeThe product was purified by column chromotography on silica gel, 4:1 hexane

Vorschrift

To a solution of 2,5-dimethylcyclopentanol (0.55 g.), compound 1 (0.97 g), and 4-(dimethylamino)pyridine (0.06 g.) in methylene chloride (100 ml) was added dicyclohexylacarbodiimide (1.09 g.), and the resulting mixture was stirred overnight. The precipitated dicyclohexylurea was removed by filtration, and the filtrate was evaporated. Ethyl acetate was then added to the residue, and the mixture was filtered again. The filtrate was washed with 1M hydrochloric acid, saturated aqeuous sodium bicarbonate, and water, dried over magnesium sulfate, and the solvent was evaporated to a colorless oil (1.18 g. 83%). The product was purified by column chromotography on silica gel, 4:1 hexane:ethyl acetate, eluent.

Quelle