反応 #1340603

反応方程式

sodium thiosulfate

Dess Martin reagent

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

→

title compound

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

溶媒

dichloromethane

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   温度Under cooling
3. 3
   抽出The aqueous layer was extracted with dichloromethane (30 mL×1)
4. 4
   洗浄the organic layer was washed sequentially by a 0.05 mol/L aqueous sodium hydroxide solution (60 mL) and saturated brine (100 mL)
5. 5
   乾燥dried over anhydrous sodium sulfate
6. 6
   ろ過After filtration
7. 7
   濃縮the filtrate was concentrated under reduced pressure

実験手順

(3S,4S)-1-Benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-hydroxymethylpyrrolidine (1.00 g, 2.85 mmol) was dissolved in dichloromethane (40 mL). Under cooling with ice, Dess Martin reagent (1.42 g, 3.42 mmol) was added thereto, and the resultant mixture was stirred at room temperature for 2 hours under a nitrogen atmosphere. Under cooling, 5% aqueous sodium thiosulfate solution (50 mL) was added thereto, followed by stirring for 0.5 hours. The aqueous layer was extracted with dichloromethane (30 mL×1), and the organic layer was washed sequentially by a 0.05 mol/L aqueous sodium hydroxide solution (60 mL) and saturated brine (100 mL), and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, to thereby yield the title compound as a colorless oily substance (0.90 g, 91%).

出典