Reaktion #1109489

Reaktionsgleichung

tert-butyl 2-hydroxyethyl(methyl)carbamate

pyridine

ethyl chlorocarbonate

→

title compound

Ethyl 2-(methylamino)ethyl carbonate hydrochloride

Lösungsmittel

ethyl acetate

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas dropwise added
2. 2
   WaschenThe mixture was washed with water (50 mL)
3. 3
   Trocknena 5% aqueous citric acid solution (50 mL) and saturated brine (50 mL), and dried over anhydrous magnesium sulfate
4. 4
   EinengenAfter concentration under reduced pressure
5. 5
   workup.ADDITIONa 4N hydrogen chloride-ethyl acetate solution (10 mL) was added to the residue
6. 6
   workup.STIRRINGAfter stirring at room temperature for 2 hrs
7. 7
   workup.ADDITION, diethyl ether (10 mL) was added
8. 8
   Filtrationthe precipitated solid was collected by filtration
9. 9
   SonstigeThe solid was dried under reduced pressure

Vorschrift

To a mixture of tert-butyl 2-hydroxyethyl(methyl)carbamate (1.75 g) obtained in Reference Example 1 and ethyl acetate (20 mL) were added pyridine (0.97 mL) and 4-dimethylaminopyridine (catalytic amount), and ethyl chlorocarbonate (1.25 mL) was dropwise added. The mixture was stirred overnight at room temperature and ethyl acetate (50 mL) was added. The mixture was washed with water (50 mL), a 5% aqueous citric acid solution (50 mL) and saturated brine (50 mL), and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, a 4N hydrogen chloride-ethyl acetate solution (10 mL) was added to the residue. After stirring at room temperature for 2 hrs., diethyl ether (10 mL) was added, and the precipitated solid was collected by filtration. The solid was dried under reduced pressure to give the title compound (1.66 g) as a white solid.

Quelle