Reaktion #11582

Reaktionsgleichung

Methanol

2-(1-Adamantyl)-N-pentylethylamine hydrochloride

diglycolyl chloride

triethylamine

→

2-methoxycarbonylmethoxyacetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide

Ausbeute 60.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   workup.STIRRINGthe whole was stirred for three hours
3. 3
   SonstigeThe solvent was evaporated under reduced pressure
4. 4
   Waschenwas washed with a saturated aqueous sodium chloride solution (5 ml)
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   SonstigeThe solvent was evaporated under reduced pressure
7. 7
   Sonstigethe resulting residue was purified by silica gel column chromatography

Vorschrift

2-(1-Adamantyl)-N-pentylethylamine hydrochloride (Intermediate No. 1-1) (0.50 g, 1.7 mmol) was added to a solution of diglycolyl chloride (0.31 ml, 2.6 mmol) and triethylamine (0.70 ml, 5.1 mmol) in anhydrous dichloromethane (6 ml) under ice-cooling, and the mixture was stirred at room temperature overnight. Methanol (5 ml) was added to the reaction mixture, and the whole was stirred for three hours. The solvent was evaporated under reduced pressure, the residue was distributed with ethyl acetate and water (15 ml respectively), and the organic layer was washed with a saturated aqueous sodium chloride solution (5 ml) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, the resulting residue was purified by silica gel column chromatography to give 0.39 g (60%) of 2-methoxycarbonylmethoxyacetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide as an oily matter.

Quelle