N-Hydroxyacetamidine → 2-[3-Methyl-1,2,4-oxadiazol-5-yl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene

HRID 1440029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1440029
[C:1](=[N:4][OH:5])([NH2:3])[CH3:2].[CH3:6][N:7]1[C@H:11]2[C:12]([C:15](OC)=O)=[CH:13][CH2:14][C@@H:8]1[CH2:9][CH2:10]2>C1COCC1>[CH3:2][C:1]1[N:3]=[C:15]([C:12]2[CH:11]3[N:7]([CH3:6])[CH:8]([CH2:14][CH:13]=2)[CH2:9][CH2:10]3)[O:5][N:4]=1

Komponenten

4

Edukt 2

HCID 30926N-HydroxyacetamidineHCID 119478(-)-Anhydroecgonine methyl ester

Produkt 1

HCID 189853812-[3-Methyl-1,2,4-oxadiazol-5-yl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Acetamide oxime (500 mg, 6.75 mmol) suspended in THF (50 mL) under nitrogen was heated at 60° C. with Nail (132 mg, 5.5 mmol in oil dispersion) for 1 h. Anhydroecgonine methyl ester (2.76 mmol) and 4 A· molecular sieves (2 g) were added and the reaction mixture heated under reflux for 3 h, After cooling, the reaction mixture was filtered and the solvent removed in vacuo. The residue was chromatographed on a silica gel column eluting with CHCl3 --CH3OH (95:5) to give the free base.

Aufarbeitung

  1. temperaturethe reaction mixture heated
  2. temperatureunder reflux for 3 h
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered
  5. customthe solvent removed in vacuo
  6. customThe residue was chromatographed on a silica gel column
  7. washeluting with CHCl3 --CH3OH (95:5)
  8. customto give the free base

Quellen und Nachweise

ORD-Eintrag
ord-85bdfb52da7044458adb59ffe68350fe
Quelldatensatz
uspto-grants-1996_03
Patentnummer
US05496953

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