Hydrochloric Acid → 3-Benzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione

HRID 1478950Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1478950
[CH2:1]([N:8]1[C:14](=[O:15])[CH:13]2[N:16](CC3C=CC=CC=3)[CH:10]([CH2:11][CH2:12]2)[C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO.[Pd]>[CH2:1]([N:8]1[C:9](=[O:24])[CH:10]2[NH:16][CH:13]([CH2:12][CH2:11]2)[C:14]1=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 166374903,8-Dibenzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione

Produkt 1

HCID 148395753-Benzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dioneAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 3,8-dibenzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione (0.00025 mol, 80 mg) in MeOH (2 mL) containing few drops of HCl was hydrogenated with 10% Pd—C (8 mg) for 4 h at room temperature. After completion of the reaction (checked by TLC), the reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure. The crude residue was purified by column chromatography (silica gel, 60-120 mesh; EA-Hexane, 6:4) to afford the 3-benzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione (LXVI) in 80% yield.

Aufarbeitung

  1. customAfter completion of the reaction (checked by TLC)
  2. filtrationthe reaction mixture was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe crude residue was purified by column chromatography (silica gel, 60-120 mesh; EA-Hexane, 6:4)

Quellen und Nachweise

ORD-Eintrag
ord-f28199fbcb92413bb69d951fa3b88281
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09404081B2

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