Reacción #41705

Ecuación de reacción

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

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawith cooling with ice
2. 2
   OtroThe reaction liquid
3. 3
   Temperaturawith cooling with ice
4. 4
   Otrothe 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
   OtroThe reaction liquid
8. 8
   Extracciónextracted with ethyl acetate
9. 9
   Secadodried with anhydrous sodium sulfate
10. 10
    OtroThe solvent was evaporated away under reduced pressure
11. 11
    Otrothe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=9/1)
12. 12
    Otroto obtain the entitled compound

Procedimiento

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.

Fuente