反応 #41705

反応方程式

borane methyl sulfide

cyclohexene

ammonium chloride

N-(3-fluoro-4-(1-hydroxy-3-methyl-3-buten-1-yl)phenyl)pyridine-2-carboxamide

sodium hydroxide

hydrogen peroxide

→

N-(4-(1,4-dihydroxy-3-methylbutyl)-3-fluorophenyl)pyridine-2-carboxamide

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   温度with cooling with ice
2. 2
   その他The reaction liquid
3. 3
   温度with cooling with ice
4. 4
   その他the reaction liquid
5. 5
   workup.STIRRINGwas stirred at room temperature for 1 hour
6. 6
   workup.STIRRINGstirred at room temperature for 10 minutes
7. 7
   その他The reaction liquid
8. 8
   抽出extracted with ethyl acetate
9. 9
   乾燥dried with anhydrous sodium sulfate
10. 10
    その他The solvent was evaporated away under reduced pressure
11. 11
    その他the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=9/1)
12. 12
    その他to obtain the entitled compound

実験手順

1.20 ml of borane-methyl sulfide complex (1 M dichloromethane solution) was added to a tetrahydrofuran (5 ml) solution of 0.082 ml of cyclohexene with cooling with ice. The reaction liquid was stirred for 10 minutes with cooling with ice, and a tetrahydrofuran (3 ml) solution of 301 mg of N-(3-fluoro-4-(1-hydroxy-3-methyl-3-buten-1-yl)phenyl)pyridine-2-carboxamide was added to it, and the reaction liquid was stirred at room temperature for 1 hour. 0.50 ml of aqueous 5 N sodium hydroxide solution and aqueous 35% hydrogen peroxide solution were added in order to the reaction liquid, and stirred at room temperature for 10 minutes. The reaction liquid was poured into an aqueous saturated ammonium chloride solution, extracted with ethyl acetate, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=9/1) to obtain the entitled compound.

出典