Reaktion #46685

Reaktionsgleichung

1-[2-(1-adamantyl)ethyl]-3-[3-(t-butyldimethylsilyloxy)-3-(4-pyridyl)propyl]-1-pentylurea

→

1-[2-(1-Adamantyl)ethyl]-3-[3-hydroxy-3-(4-pyridyl)propyl]-1-pentylurea

Lösungsmittel

hydrogen chloride methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was evaporated under reduced pressure
2. 2
   WaschenThe organic layer was washed with a saturated aqueous sodium chloride solution (40 ml)
3. 3
   Trocknendried over anhydrous sodium sulfate
4. 4
   SonstigeThe solvent was evaporated under reduced pressure
5. 5
   Sonstigethe residue was purified by silica gel column chromatography
6. 6
   Sonstigeto give the target compound (59.2 mg, colorless amorphous powder, 55.3%)

Vorschrift

A solution of 1-[2-(1-adamantyl)ethyl]-3-[3-(t-butyldimethylsilyloxy)-3-(4-pyridyl)propyl]-1-pentylurea (Compound No. 1-138, 136 mg, 0.250 mmol) in 10% hydrogen chloride-methanol (2.3 ml) was stirred at room temperature for three days. The solvent was evaporated under reduced pressure, and the residue was distributed between ethyl acetate (50 ml), water (30 ml) and a 1 N aqueous sodium hydroxide solution (20 ml). The organic layer was washed with a saturated aqueous sodium chloride solution (40 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the target compound (59.2 mg, colorless amorphous powder, 55.3%).

Quelle