Reaction #172389

Reaction equation

hydrogen peroxide

9-borabicyclo[3.3.1]nonane

compound

1-(2-Methoxy-4-nitrophenyl)-3-vinylpyridin-2(1H)-one

sodium disulphite

sodium hydroxide

→

3-(2-Hydroxyethyl)-1-(2-methoxy-4-nitrophenyl)pyridin-2(1H)-one

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   workup.WAITAfter a further hour at this temperature
2. 2
   Otherdoes not exceed 30° C
3. 3
   TemperatureCooling
4. 4
   Otheris removed
5. 5
   workup.STIRRINGthe mixture is stirred for another 30 min
6. 6
   ExtractionThe mixture is extracted repeatedly with ethyl acetate
7. 7
   Otherthe organic phase is separated off
8. 8
   WashThe combined organic phases are washed with saturated sodium chloride solution
9. 9
   Dryingdried over magnesium sulphate
10. 10
    Otherevaporated to dryness under reduced pressure
11. 11
    OtherThe residue is absorbed on silica gel
12. 12
    Otherchromatographed
13. 13
    Otherevaporated to dryness under reduced pressure
14. 14
    OtherFor crystallization, tert-butyl methyl ether
15. 15
    workup.ADDITIONis added
16. 16
    FiltrationThe crystals are filtered off
17. 17
    Otherdried under reduced pressure

Procedure

At 0° C., a solution of 36 g (299 mmol) of 9-borabicyclo[3.3.1]nonane in 600 ml of tetrahydrofuran is added over a period of 45 min to 37 g (136 mmol) of the compound from Example 20A. After a further hour at this temperature, a solution of 27 g (680 mmol) of sodium hydroxide (1N in water) is added over the course of 15 min. The mixture is stirred for a further 5 min, and 125 ml of a 30% strength hydrogen peroxide solution are then added such that the temperature does not exceed 30° C. Cooling is removed, and the mixture is stirred for another 30 min. The mixture is extracted repeatedly with ethyl acetate, the combined organic phases are washed with a solution of 730 g (1.50 mol) of sodium disulphite, the organic phase is separated off and the aqueous phase is reextracted with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulphate and evaporated to dryness under reduced pressure. The residue is absorbed on silica gel and chromatographed using a gradient of cyclohexane and ethyl acetate. The product fractions are combined and evaporated to dryness under reduced pressure. For crystallization, tert-butyl methyl ether is added. The crystals are filtered off and dried under reduced pressure. This gives 24 g (60% of theory) of the desired product.

Source