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

HRID 1786255

Reaktionsgleichung

Reaktionsgleichung von HRID 1786255
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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 21862267Methyl 2-{3-hydroxy-1-azabicyclo[2.2.2]octan-3-yl}acetateAusbeute 48,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-580edcc21b3943089555aff97a359acc
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07507744B2

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