Реакция #46685

Уравнение реакции

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

Растворители

hydrogen chloride methanol

Условия реакции

Обработка

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

Методика

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%).

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