Reacción #172389

Ecuación de reacción

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

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITAfter a further hour at this temperature
2. 2
   Otrodoes not exceed 30° C
3. 3
   TemperaturaCooling
4. 4
   Otrois removed
5. 5
   workup.STIRRINGthe mixture is stirred for another 30 min
6. 6
   ExtracciónThe mixture is extracted repeatedly with ethyl acetate
7. 7
   Otrothe organic phase is separated off
8. 8
   LavadoThe combined organic phases are washed with saturated sodium chloride solution
9. 9
   Secadodried over magnesium sulphate
10. 10
    Otroevaporated to dryness under reduced pressure
11. 11
    OtroThe residue is absorbed on silica gel
12. 12
    Otrochromatographed
13. 13
    Otroevaporated to dryness under reduced pressure
14. 14
    OtroFor crystallization, tert-butyl methyl ether
15. 15
    workup.ADDITIONis added
16. 16
    FiltraciónThe crystals are filtered off
17. 17
    Otrodried under reduced pressure

Procedimiento

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.

Fuente