Reaktion #41663

Reaktionsgleichung

sodium bicarbonate

triethylamine

methanesulfonyl chloride

N-(4-(2-((t-butyl(dimethyl)silyl)oxy)-1,4-dihydroxybutyl)-3-fluorophenyl)pyridine-2-carboxamide

→

N-(4-(3-((t-butyl(dimethyl)silyl)oxy)pyrrolidin-2-yl)-3-fluorophenyl)pyridine-2-carboxamide

Lösungsmittel

water

chloroform

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwith cooling with ice
2. 2
   Sonstigethe reaction liquid
3. 3
   SonstigeThe reaction liquid
4. 4
   Waschenwashed with aqueous saturated sodium bicarbonate
5. 5
   Trocknendried with anhydrous sodium sulfate
6. 6
   SonstigeThe solvent was evaporated away under reduced pressure, and 25 mg of sodium azide
7. 7
   workup.ADDITIONwas added to a dimethylformamide (5 ml) solution of the resulting residue
8. 8
   Sonstigethe reaction liquid
9. 9
   workup.STIRRINGwas stirred at 40° C. for 2 hours
10. 10
    SonstigeThe reaction liquid
11. 11
    Temperaturwas cooled
12. 12
    Extraktionextracted with ethyl acetate
13. 13
    Trocknendried with anhydrous sodium sulfate
14. 14
    SonstigeThe solvent was evaporated away under reduced pressure, and 50 mg of sodium borohydride and 5 mg of copper sulfate pentahydrate
15. 15
    workup.ADDITIONwere added in order to a methanol (10 ml) solution of the resulting residue
16. 16
    Sonstigethe reaction liquid
17. 17
    workup.STIRRINGwas stirred at 40° C. for 2 hours
18. 18
    SonstigeThe reaction liquid
19. 19
    Temperaturwas cooled
20. 20
    Extraktionextracted with chloroform
21. 21
    Trocknendried with anhydrous sodium sulfate
22. 22
    SonstigeThe solvent was evaporated away under reduced pressure
23. 23
    Sonstigethe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=50/1)
24. 24
    Sonstigeto obtain the entitled compound as a colorless oily substance

Vorschrift

155 mg of triethylamine and 130 mg of methanesulfonyl chloride were added in order to a chloroform (8 ml) solution of 165 mg of N-(4-(2-((t-butyl(dimethyl)silyl)oxy)-1,4-dihydroxybutyl)-3-fluorophenyl)pyridine-2-carboxamide, with cooling with ice, and the reaction liquid was stirred at room temperature for 30 minutes. The reaction liquid was diluted with chloroform, washed with aqueous saturated sodium bicarbonate, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and 25 mg of sodium azide was added to a dimethylformamide (5 ml) solution of the resulting residue, and the reaction liquid was stirred at 40° C. for 2 hours. The reaction liquid was cooled, water was added to it, extracted with ethyl acetate, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and 50 mg of sodium borohydride and 5 mg of copper sulfate pentahydrate were added in order to a methanol (10 ml) solution of the resulting residue, and the reaction liquid was stirred at 40° C. for 2 hours. The reaction liquid was cooled, aqueous saturated sodium bicarbonate was added to it, extracted with chloroform, 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=50/1) to obtain the entitled compound as a colorless oily substance.

Quelle