Reaktion #11563

Reaktionsgleichung

hydrogen chloride

1-[2-(1-adamantyl)ethyl]-1-[2-(t-butoxycarbonyl)ethyl]-3-[3-(4-pyridyl)propyl]urea

hydrogen chloride

ethyl acetate

→

titled compound

Ausbeute 79.0%

1-[2-(1-Adamantyl)ethyl]-3-[3-(4-pyridyl)propyl]hexahydro-2,4-pyrimidinedione hydrochloride

Ausbeute 79.0%

Lösungsmittel

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated under reduced pressure
2. 2
   workup.ADDITIONa 1 N aqueous sodium hydroxide solution (20 ml) and ethyl acetate (30 ml) were added to the residue, and layers
3. 3
   Sonstigewere separated
4. 4
   WaschenThe ethyl acetate layer was washed with water (20 ml)
5. 5
   Trocknena saturated aqueous sodium chloride solution (20 ml) successively and dried over anhydrous magnesium sulfate
6. 6
   EinengenThe ethyl acetate layer was concentrated under reduced pressure
7. 7
   workup.DISSOLUTIONthe resulting oily matter was dissolved in diethyl ether (20 ml)
8. 8
   Temperaturunder ice-cooling
9. 9
   Einengenthe mixture was concentrated under reduced pressure
10. 10
    Filtrationthe precipitated solid was filtered off with ethyl acetate

Vorschrift

A 4 N solution of hydrogen chloride in 1,4-dioxane (2.5 ml) was added to 1-[2-(1-adamantyl)ethyl]-1-[2-(t-butoxycarbonyl)ethyl]-3-[3-(4-pyridyl)propyl]urea (Compound No. 1-69) (0.23 g, 0.49 mmol), and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, a 1 N aqueous sodium hydroxide solution (20 ml) and ethyl acetate (30 ml) were added to the residue, and layers were separated. The ethyl acetate layer was washed with water (20 ml) and a saturated aqueous sodium chloride solution (20 ml) successively and dried over anhydrous magnesium sulfate. The ethyl acetate layer was concentrated under reduced pressure, and the resulting oily matter was dissolved in diethyl ether (20 ml). A 4 N solution of hydrogen chloride in ethyl acetate (0.50 ml, 2.00 mol) was added thereto under ice-cooling, the mixture was concentrated under reduced pressure, and the precipitated solid was filtered off with ethyl acetate to give 0.17 g (79%) of the titled compound.

Quelle