Reaction #172400

Reaction equation

sodium hydroxide

hydrogen peroxide

9-borabicyclo[3.3.1]nonane

compound

3-Allyl-1-(2-methyl-4-nitrophenyl)pyridin-2(1H)-one

sodium bisulphite

→

3-(3-Hydroxypropyl)-1-(2-methyl-4-nitrophenyl)pyridin-2(1H)-one

Solvents

water

THF

THF

ethyl acetate

Conditions

Workup

1. 1
   Otherdoes not exceed 30° C
2. 2
   workup.STIRRINGThe mixture is stirred with ice-
3. 3
   Temperaturecooling for 30 min
4. 4
   OtherThe organic phase is separated off
5. 5
   Extractionthe aqueous phase is extracted twice with ethyl acetate
6. 6
   WashThe combined organic phases are washed with saturated aqueous sodium chloride solution
7. 7
   DryingThe organic phase is dried over sodium sulphate
8. 8
   Otherevaporated to dryness under reduced pressure
9. 9
   OtherThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 1:4)

Procedure

At 0° C., 18.5 ml (9.25 mmol) of a 0.5 molar solution of 9-borabicyclo[3.3.1]nonane in THF are slowly added dropwise to 1.00 g (3.70 mmol) of the compound from Example 35A in 4 ml THF. After one hour at room temperature, the mixture is again cooled to 0° C., and 18.5 ml (18.5 mmol) of a 1 molar solution of sodium hydroxide in water are added dropwise. The mixture is stirred at 0° C. for a further 30 min, and 3.24 ml of a 30% strength hydrogen peroxide solution are then added such that the temperature does not exceed 30° C. The mixture is stirred with ice-cooling for 30 min, and ethyl acetate and then 11 g (40 mmol) of sodium bisulphite solution are then added. The organic phase is separated off, and the aqueous phase is extracted twice with ethyl acetate. The combined organic phases are washed with saturated aqueous sodium chloride solution. The organic phase is dried over sodium sulphate and then evaporated to dryness under reduced pressure. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 1:4). This gives 1.03 g (83% of theory) of the desired product.

Source