反応 #46289
ord-3bbc7e5ac5a74798ab3ef4002e1dcdfe
反応方程式
反応物
試薬
反応条件
後処理
- 1洗浄The product mixture was washed successively with aqueous NaHCO3, water, and brine
- 2抽出The organic extract
- 3乾燥was dried over anhydrous sodium sulfate
- 4ろ過filtered
- 5濃縮concentrated under vacuum
- 6その他This intermediate silylated aminoalcohol was used without further purification
- 7濃縮The reaction mixture was concentrated under vacuum
- 8その他The residue was partitioned between ethyl acetate and aqueous sodium carbonate
- 9抽出The organic extract
- 10乾燥was dried over anhydrous sodium sulfate
- 11ろ過filtered
- 12濃縮concentrated under vacuum
- 13その他Collection and concentration of appropriate fractions
実験手順
A mixture of 4-hydroxybutylamine (4.0 g, 44.9 mmol), tert-butyldimethyl-silyl chloride (7.4 g, 49.3 mmol) and imidazole (6.7 g, 98.7 mmol) in dichloromethane (150 mL) was stirred at room temperature for 2 hours. The product mixture was washed successively with aqueous NaHCO3, water, and brine. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. This intermediate silylated aminoalcohol was used without further purification. To a mixture of the amine (1.0 g, 4.9 mmol) and benzyloxyacetaldehyde (0.74 g, 4.9 mmol) in dichloroethane (15 mL) at room temperature, sodium triacetoxyborohydride (1.3 g, 6.3 mmol) was added. The reaction mixture was concentrated under vacuum. The residue was partitioned between ethyl acetate and aqueous sodium carbonate. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 2% methanol in dichloromethane. Collection and concentration of appropriate fractions afforded the title silyloxybutyl-amine.