반응 #76781

반응 방정식

Trifluoroacetic acid

2-(3-hydroxy-1-azabicyclo[2.2.2]oct-3-yl)acetic acid t-butyl ester

→

tan crystalline subtitle compound

수율 48.6%

2-(3-Hydroxy-1-azabicyclo[2.2.2]oct-3-yl)acetic acid methyl ester

수율 48.6%

용매

dichloromethane

반응 조건

후처리

1. 1
   기타the solvent was evaporated under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in methanol (90 mL)
3. 3
   온도cooled in an ice bath
4. 4
   workup.ADDITIONConcentrated sulfuric acid (9 mL) was added dropwise over 10 minutes
5. 5
   workup.STIRRINGthe reaction mixture was stirred at room temperature
6. 6
   workup.WAITAfter 3 hours
7. 7
   workup.ADDITIONthe solution was poured into 100 mL of ice water
8. 8
   추출extracted with chloroform (4×100 mL)
9. 9
   건조The extracts were dried (MgSO4)
10. 10
    여과filtered
11. 11
    기타evaporated in vacuo
12. 12
    기타to give a solid
13. 13
    기타Recrystallization from ethyl acetate

실험 절차

Trifluoroacetic acid (40 mL) was added dropwise over 15 minutes to a solution of 2-(3-hydroxy-1-azabicyclo[2.2.2]oct-3-yl)acetic acid t-butyl ester (15.7 g) in anhydrous dichloromethane (40 mL) at 0° C. The mixture was stirred for 24 hours at room temperature, then the solvent was evaporated under reduced pressure. The residue was dissolved in methanol (90 mL) and cooled in an ice bath. Concentrated sulfuric acid (9 mL) was added dropwise over 10 minutes, then the reaction mixture was stirred at room temperature. After 3 hours, the solution was poured into 100 mL of ice water, basified to pH 10 with saturated aqueous sodium carbonate solution, and extracted with chloroform (4×100 mL). The extracts were dried (MgSO4), filtered, and evaporated in vacuo to give a solid. Recrystallization from ethyl acetate provided 6.3 g of the tan crystalline subtitle compound.

출처