تفاعل #11571

معادلة التفاعل

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

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titled compound

المردود 55.3%

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

المردود 55.3%

المذيبات

hydrogen chloride methanol

ظروف التفاعل

المعالجة

1. 1
   أخرىThe solvent was evaporated under reduced pressure
2. 2
   غسيلa 1 N aqueous sodium hydroxide solution (20 ml), and the organic layer was washed with a saturated aqueous sodium chloride solution (40 ml)
3. 3
   تجفيفThe organic layer was dried over anhydrous sodium sulfate
4. 4
   أخرىthe solvent was evaporated under reduced pressure
5. 5
   أخرىthe residue was purified by silica gel column chromatography

الإجراء التجريبي

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, the residue was distributed with ethyl acetate (50 ml), water (30 ml) and a 1 N aqueous sodium hydroxide solution (20 ml), and the organic layer was washed with a saturated aqueous sodium chloride solution (40 ml). The organic layer was 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 titled compound (59.2 mg, colorless noncrystalline powder, 55.3%).

المصدر