Реакция #41627

Уравнение реакции

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

Растворители

chloroform

chloroform

triethylamine

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Другоеthe reaction liquid
2. 2
   ДругоеThe reaction liquid
3. 3
   Промывкаwashed with aqueous saturated sodium bicarbonate, aqueous saturated sodium thiosulfate and saturated saline in order
4. 4
   Сушкаdried with anhydrous sodium sulfate
5. 5
   ДругоеThe solvent was evaporated away under reduced pressure
6. 6
   Другоеto obtain a crude product
7. 7
   Другоеthe reaction liquid
8. 8
   workup.STIRRINGwas stirred at room temperature for 15 minutes
9. 9
   ДругоеThe 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
    Другоеthe reaction liquid
12. 12
    workup.STIRRINGwas stirred at room temperature for 15 minutes
13. 13
    ДругоеThe solvent was evaporated away under reduced pressure
14. 14
    Другоеthe residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=30/1)

Методика

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.

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