Dimethylformamide dimethyl acetal → tert-butyl 3-[(dimethylamino)methylene]-4-oxotetrahydro-1(2H)-pyridinecarboxylate

HRID 132858

Reaktionsgleichung

Reaktionsgleichung von HRID 132858
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>CN(C)C=O>[O:1]=[C:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][C:7]1=[CH:17][N:18]([CH3:20])[CH3:19]

Komponenten

4

Edukt 2

HCID 78373Dimethylformamide dimethyl acetalHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Produkt 1

HCID 53395404tert-butyl 3-[(dimethylamino)methylene]-4-oxotetrahydro-1(2H)-pyridinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of tert-butyl 4-oxo-1-piperidinecarboxylate (8.73 g, 44 mmol) and N,N-dimethylformamide dimethyl acetal (5.8 mL, 44 mmol) in 80 mL of dry N,N-dimethylformamide was warmed at 80° C. for 18 h. The solution was cooled and concentrated under reduced pressure, and the residue was partitioned between ethyl acetate and water. The mixture was filtered through a pad of Celite, and the organic layer was separated, washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure to afford the title compound as an orange oil.

Aufarbeitung

  1. temperatureThe solution was cooled
  2. concentrationconcentrated under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and water
  4. filtrationThe mixture was filtered through a pad of Celite
  5. customthe organic layer was separated
  6. washwashed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-eaf1fa1683814914835bc4295fe62e17
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07388019B2

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