Trifluoroacetic acid → Benzyl piperidine-3-carboxylate

HRID 602126Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 602126
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:30][CH2:29][CH2:28][CH:17]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:16]1)=O)(C)(C)C>ClCCl>[NH:15]1[CH2:30][CH2:29][CH2:28][CH:17]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:16]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 20723878Benzyl 1-Boc-piperidine-3-carboxylate

Produkt 1

HCID 13419237Benzyl piperidine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (43 mL, 558 mmol) was added to benzyl 1-(tert-butoxycarbonyl)nipecotate (7.11 g, 22.3 mmol) in dichloromethane (20 mL). The mixture was stirred for 3 hours. Subsequently, the reaction mixture was concentrated and water was added to the residue, followed by addition of 1 mol/L aqueous sodium hydroxide solution to make the mixture basic. The mixture was then extracted with ethyl acetate. The organic layer washed with brine and was dried over sodium sulfate. The solvent was evaporated to give 5.97 g (quant.) of the desired compound as a yellow oil.

Aufarbeitung

  1. concentrationSubsequently, the reaction mixture was concentrated
  2. additionwater was added to the residue
  3. additionfollowed by addition of 1 mol/L aqueous sodium hydroxide solution
  4. extractionThe mixture was then extracted with ethyl acetate
  5. washThe organic layer washed with brine
  6. dry with materialwas dried over sodium sulfate
  7. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-139d2dd9afb445229f6e8c7ed36bbaa0
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902367B2

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