Reaction #41705

Reaction equation

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

Solvents

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   Temperaturewith cooling with ice
2. 2
   OtherThe reaction liquid
3. 3
   Temperaturewith cooling with ice
4. 4
   Otherthe 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
   OtherThe reaction liquid
8. 8
   Extractionextracted with ethyl acetate
9. 9
   Dryingdried with anhydrous sodium sulfate
10. 10
    OtherThe solvent was evaporated away under reduced pressure
11. 11
    Otherthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=9/1)
12. 12
    Otherto obtain the entitled compound

Procedure

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.

Source