Reacción #77878

Ecuación de reacción

Trifluoroacetic acid

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

→

tan crystalline subtitle compound

Rendimiento 48.6%

2-(3-Hydroxy-1-azabicyclo[2.2.2]oct-3-yl)acetic Acid Methyl Ester

Rendimiento 48.6%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe solvent was evaporated under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in methanol (90 mL)
3. 3
   Temperaturacooled 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
   Extracciónextracted with chloroform (4×100 mL)
9. 9
   SecadoThe extracts were dried (MgSO4)
10. 10
    Filtraciónfiltered
11. 11
    Otroevaporated in vacuo
12. 12
    Otroto give a solid
13. 13
    OtroRecrystallization from ethyl acetate

Procedimiento

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.

Fuente