反応 #41627

反応方程式

acetic anhydride

water

iodine

N-(1-(2-fluoro-4-nitro-phenyl)-3-butenyl)-acetamide

→

compound

1-acetyl-2-(2-fluoro-4-nitro-phenyl)-4-hydroxy-pyrrolidine

溶媒

chloroform

chloroform

triethylamine

tetrahydrofuran

反応条件

後処理

1. 1
   その他the reaction liquid
2. 2
   その他The reaction liquid
3. 3
   洗浄washed with aqueous saturated sodium bicarbonate, aqueous saturated sodium thiosulfate and saturated saline in order
4. 4
   乾燥dried with anhydrous sodium sulfate
5. 5
   その他The solvent was evaporated away under reduced pressure
6. 6
   その他to obtain a crude product
7. 7
   その他the reaction liquid
8. 8
   workup.STIRRINGwas stirred at room temperature for 15 minutes
9. 9
   その他The solvent was evaporated away under reduced pressure, 20 mg of potassium carbonate
10. 10
    workup.ADDITIONwas added to a methanol (5 ml) solution of the resulting residue
11. 11
    その他the reaction liquid
12. 12
    workup.STIRRINGwas stirred at room temperature for 15 minutes
13. 13
    その他The solvent was evaporated away under reduced pressure
14. 14
    その他the residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=30/1)

実験手順

1 ml of water and 600 mg of iodine were added to a tetrahydrofuran (4 ml) solution of 200 mg of N-(1-(2-fluoro-4-nitro-phenyl)-3-butenyl)-acetamide, and the reaction liquid was stirred overnight at room temperature. The reaction liquid was diluted with chloroform, washed with aqueous saturated sodium bicarbonate, aqueous saturated sodium thiosulfate and saturated saline in order, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure to obtain a crude product. 0.25 ml of triethylamine, 0.13 ml of acetic anhydride and 10 mg of 4-dimethylaminopyridine were added to a chloroform (5 ml) solution of the crude product, and the reaction liquid was stirred at room temperature for 15 minutes. The solvent was evaporated away under reduced pressure, 20 mg of potassium carbonate was added to a methanol (5 ml) solution of the resulting residue, and the reaction liquid was stirred at room temperature for 15 minutes. The solvent was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=30/1) to obtain the entitled compound as a colorless solid diastereomer mixture.

出典