Trifluoroacetic acid → Methyl 2-{3-hydroxy-1-azabicyclo[2.2.2]octan-3-yl}acetate

HRID 48503

반응식

HRID 48503 반응식
FC(F)(F)C(O)=O.[C:8]([O:12][C:13](=[O:24])[CH2:14][C:15]1([OH:23])[CH:20]2[CH2:21][CH2:22][N:17]([CH2:18][CH2:19]2)[CH2:16]1)(C)(C)C>ClCCl>[CH3:8][O:12][C:13](=[O:24])[CH2:14][C:15]1([OH:23])[CH:20]2[CH2:21][CH2:22][N:17]([CH2:18][CH2:19]2)[CH2:16]1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 453576912-(3-Hydroxy-1-azabicyclo[2.2.2]oct-3-yl)acetic acid t-butyl ester

생성물 1

HCID 21862267Methyl 2-{3-hydroxy-1-azabicyclo[2.2.2]octan-3-yl}acetate수율 48.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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.

후처리

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in methanol (90 mL)
  3. temperaturecooled in an ice bath
  4. additionConcentrated sulfuric acid (9 mL) was added dropwise over 10 minutes
  5. stirringthe reaction mixture was stirred at room temperature
  6. waitAfter 3 hours
  7. additionthe solution was poured into 100 mL of ice water
  8. extractionextracted with chloroform (4×100 mL)
  9. dry with materialThe extracts were dried (MgSO4)
  10. filtrationfiltered
  11. customevaporated in vacuo
  12. customto give a solid
  13. customRecrystallization from ethyl acetate

출처 및 근거

ORD 기록
ord-bec9c82dfbf84a6c8212e47e29156169
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06703502B2

연결된 노트

불러오는 중…