反応 #1340610
ord-07800dddeecd46699471d0127fe6f142
反応方程式
反応物
反応条件
後処理
- 1workup.WAITfurther at 40° C. for 5 minutes
- 2workup.STIRRINGby stirring at room temperature for 10 hours
- 3抽出The obtained aqueous layer was extracted with ethyl acetate (100 mL×2)
- 4洗浄The combined organic layer was washed sequentially by saturated sodium hydrogencarbonate (100 mL) and saturated brine (100 mL)
- 5乾燥dried over anhydrous sodium sulfate
- 6ろ過After filtration
- 7濃縮the filtrate was concentrated under reduced pressure
- 8その他The obtained residue was purified through silica gel column chromatography (ethyl acetate:n-hexane=1:4)
実験手順
Butyl lithium (3.56 mL, 1.58 M, toluene solution) was added dropwise under cooling with ice to a suspension of methyltriphenylphosphonium bromide (2.15 g, 6.03 mmol) in tetrahydrofuran (20 mL), followed by stirring at room temperature for 20 minutes, and further at 40° C. for 5 minutes. Subsequently, a solution of (3S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-formylpyrrolidine [an isomer mixture of (4S)-form:(4R)-form (1:3)] (700 mg, 2.01 mmol) in tetrahydrofuran (7.0 mL) was added under cooling with ice to the resultant mixture, followed by stirring at room temperature for 10 hours. The reaction mixture was poured to a 10% aqueous citric acid solution (20 mL), and the resultant mixture was diluted with ethyl acetate (100 mL). The obtained aqueous layer was extracted with ethyl acetate (100 mL×2). The combined organic layer was washed sequentially by saturated sodium hydrogencarbonate (100 mL) and saturated brine (100 mL), and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The obtained residue was purified through silica gel column chromatography (ethyl acetate:n-hexane=1:4), to thereby yield the title compound (an isomer mixture of (4S)-form and (4R)-form (1:4)) as a colorless oily substance (250 mg, 36%).