Reaktion #58036

Reaktionsgleichung

4-[N-(tert-butoxycarbonyl)amino]-cyclohexane carboxylic acid

O,N-dimethylhydroxylamine

DCC

triethylamine

→

[4-(methoxy-methyl-carbamoyl)-cyclohexyl]-carbamic acid tert-butyl ester

Ausbeute 61.0%

Lösungsmittel

Water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture was extracted with CHCl3
2. 2
   WaschenThe organic phase was washed with water
3. 3
   Sonstigedried
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   SonstigePurification by flash chromatography (hexane/EtOAc 1:1)

Vorschrift

A solution of 4-[N-(tert-butoxycarbonyl)amino]-cyclohexane carboxylic acid (11.95 g, 49.0 mmol), O,N-dimethylhydroxylamine (4.88 g, 50.0 mmol), DCC (9.60 g, 50 mmol) and triethylamine (5.06 g, 50.0 mmol) in DMF (150 mL) was stirred at room temperature overnight. Water (500 mL) was added and the mixture was extracted with CHCl3. The organic phase was washed with water, dried and concentrated under reduced pressure. Purification by flash chromatography (hexane/EtOAc 1:1) gave [4-(methoxy-methyl-carbamoyl)-cyclohexyl]-carbamic acid tert-butyl ester (8.50 g, 61%).

Quelle