反応 #1340600

反応方程式

methyllithium

diethyl ether

(3S,4S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-(p-toluenesulfonyloxy)methylpyrrolidine

diethyl ether

ammonium chloride

ammonia

→

title compound

(3S,4S)-1-Benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-ethylpyrrolidine

溶媒

water

反応条件

後処理

1. 1
   温度Under cooling with ice
2. 2
   workup.STIRRINGby stirring for 1 hour
3. 3
   温度under cooling with ice
4. 4
   温度Under cooling with ice
5. 5
   抽出followed by extraction with ethyl acetate (300 mL×2)
6. 6
   洗浄The combined organic layer was washed by saturated brine (100 mL)
7. 7
   乾燥dried over anhydrous sodium sulfate
8. 8
   濃縮The filtrate was concentrated under reduced pressure
9. 9
   その他The residue was purified through silica gel column chromatography (ethyl acetate:n-hexane=1:3 to 1:2)

実験手順

Under cooling with ice, a solution of methyllithium (121 mL, 1.02 M, diethyl ether solution) was added to a suspension of copper(I) iodide (11.8 g, 62.1 mmol) in diethyl ether (200 mL), followed by stirring for 30 minutes. The temperature of the reaction mixture was cooled to −78° C. A solution of (3S,4S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-(p-toluenesulfonyloxy)methylpyrrolidine (6.27 g, 12.4 mmol) in diethyl ether (140 mL) was added thereto. The temperature of the mixture was elevated gradually, followed by stirring for 1 hour under cooling with ice. Under cooling with ice, a saturated aqueous ammonium chloride solution (100 mL) and 28% aqueous ammonia (25 mL) were added to the resultant mixture, and then water (100 mL) was added thereto, followed by extraction with ethyl acetate (300 mL×2). The combined organic layer was washed by saturated brine (100 mL), and dried over anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure. The residue was purified through silica gel column chromatography (ethyl acetate:n-hexane=1:3 to 1:2), to thereby yield the title compound as a colorless oily substance (3.09 g, 71%).

出典