Reaktion #11531

Reaktionsgleichung

hydrogen chloride

ethyl acetate

triethylamine

t-butyl acrylate

2-(1-Adamantyl)ethylamine hydrochloride

→

titled compound

Ausbeute 23.0%

t-Butyl 3-[N-[2-(1-adamantyl)ethyl]amino]propionate hydrochloride

Ausbeute 23.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   EinengenThe reaction mixture was concentrated under reduced pressure
3. 3
   workup.ADDITIONa 1 N aqueous sodium hydroxide solution (30 ml) and ethyl acetate (50 ml) were added to the residue, and layers
4. 4
   Sonstigewere separated
5. 5
   WaschenThe ethyl acetate layer was washed with water (50 ml)
6. 6
   Trocknena saturated aqueous sodium chloride solution (50 ml) successively and dried over anhydrous magnesium sulfate
7. 7
   EinengenThe ethyl acetate layer was concentrated under reduced pressure
8. 8
   Sonstigethe concentrate was purified by silica gel column chromatography
9. 9
   workup.DISSOLUTIONThe resulting oily matter (0.50 g, 1.6 mmol) was dissolved in diethyl ether (20 ml)
10. 10
    Sonstigeto precipitate a solid
11. 11
    FiltrationThis solid was filtered off with diethyl ether

Vorschrift

2-(1-Adamantyl)ethylamine hydrochloride (1.0 g, 4.6 mmol) was dissolved in ethanol (10 ml), and triethylamine (0.65 ml, 4.6 mmol) and t-butyl acrylate (0.75 ml, 5.1 mmol) were added to the solution under ice-cooling. Then, the temperature was raised to room temperature, and the mixture was stirred overnight. The reaction mixture was concentrated under reduced pressure, a 1 N aqueous sodium hydroxide solution (30 ml) and ethyl acetate (50 ml) were added to the residue, and layers were separated. The ethyl acetate layer was washed with water (50 ml) and a saturated aqueous sodium chloride solution (50 ml) successively and dried over anhydrous magnesium sulfate. The ethyl acetate layer was concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography. The resulting oily matter (0.50 g, 1.6 mmol) was dissolved in diethyl ether (20 ml), and a 4 N solution of hydrogen chloride in ethyl acetate (1.0 ml, 4.0 mmol) was added thereto to precipitate a solid. This solid was filtered off with diethyl ether to give 0.33 g (23%) of the titled compound.

Quelle