2,4-Octanedione → 3,8-Dibenzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione

HRID 336129Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 336129
CC(=O)CC(=O)CCCC.[CH2:11]([N:18]1[CH:22]([C:23](=[O:32])[NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:21][CH2:20][CH:19]1[C:33](OCC)=[O:34])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:25]([N:24]1[C:33](=[O:34])[CH:19]2[N:18]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:22]([CH2:21][CH2:20]2)[C:23]1=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

3

Edukt 2

HCID 841922,4-OctanedioneHCID 59813968Ethyl 1-benzyl-5-(benzylcarbamoyl)pyrrolidine-2-carboxylate

Produkt 1

HCID 166374903,8-Dibenzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dioneAusbeute 40 %

Reaktionsbedingungen

Temperatur
215 °C

Versuchsvorschrift

2.1]octane-2,4-dione (LXVI). Ethyl 1-benzyl-5-(benzylcarbamoyl)pyrrolidine-2-carboxylate (LXV, 0.00122 mol, 450 mg) was heated under stirring at 210-220° C. for 3 h under atmospheric pressure and the formed ethyl alcohol was collected. After completion of the reaction (checked by TLC), the reaction mixture was cooled at room temperature and the residue was purified by column chromatography (silica gel, 60-120 mesh; EA-Hexane, 2:8) to afford the 3,8-dibenzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione in 40-45% yield.

Aufarbeitung

  1. customthe formed ethyl alcohol was collected
  2. customAfter completion of the reaction (checked by TLC)
  3. temperaturethe reaction mixture was cooled at room temperature
  4. customthe residue was purified by column chromatography (silica gel, 60-120 mesh; EA-Hexane, 2:8)

Quellen und Nachweise

ORD-Eintrag
ord-afd1ce3accef4a24a6a29682313a7dae
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889667B2

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