反応 #76781

反応方程式

Trifluoroacetic acid

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

→

tan crystalline subtitle compound

収率 48.6%

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

収率 48.6%

溶媒

dichloromethane

反応条件

後処理

1. 1
   その他the solvent was evaporated under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in methanol (90 mL)
3. 3
   温度cooled 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
   抽出extracted with chloroform (4×100 mL)
9. 9
   乾燥The extracts were dried (MgSO4)
10. 10
    ろ過filtered
11. 11
    その他evaporated in vacuo
12. 12
    その他to give a solid
13. 13
    その他Recrystallization from ethyl acetate

実験手順

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.

出典