Ethyl Acetate → (E)-tert-butyl 4-hydroxy-4-(4,4,4-trifluorobut-1-enyl)piperidine-1-carboxylate

HRID 514867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 514867
C([O:4][C:5]1(/[CH:18]=[CH:19]/[CH2:20][C:21]([F:24])([F:23])[F:22])[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)(=O)C.[OH-].[Na+].CC(=O)OCC>CO>[OH:4][C:5]1(/[CH:18]=[CH:19]/[CH2:20][C:21]([F:24])([F:22])[F:23])[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:15])[CH3:16])=[O:12])[CH2:9][CH2:10]1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 90447582HCID 90447582, Verbindung

Produkt 1

HCID 90447581(E)-tert-butyl 4-hydroxy-4-(4,4,4-trifluorobut-1-enyl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a mixture of (E)-tert-butyl 4-acetoxy-4-(4,4,4-trifluorobut-1-enyl)piperidine-1-carboxylate (200 mg, 0.57 mmol) in methanol (5 mL) was added 2M NaOH (2 mL, 4 mmol), the mixture was held stirring at r.t. for 16 hrs, when TLC (20% EA/PE) indicated completion of the reaction. The mixture was concentrated in vacuo, the residue was diluted with brine and extracted with EtOAc, and the organic layer was concentrated in vacuo to get the crude product, which was used directly for the next step.

Aufarbeitung

  1. customcompletion of the reaction
  2. concentrationThe mixture was concentrated in vacuo
  3. additionthe residue was diluted with brine
  4. extractionextracted with EtOAc
  5. concentrationthe organic layer was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f3c1b37c56bb4fe69ef73011534af4e4
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108921B2

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