Tetrahydrofuran → 2-Methyl-1-azabicyclo(2.2.2)octan-3-one

HRID 347658

Reaktionsgleichung

Reaktionsgleichung von HRID 347658
[CH2:1]=[C:2]1[C:7](=[O:8])[CH:6]2[CH2:9][CH2:10][N:3]1[CH2:4][CH2:5]2.C1COCC1>CO.CCOCC.[Pd]>[CH3:1][CH:2]1[C:7](=[O:8])[CH:6]2[CH2:9][CH2:10][N:3]1[CH2:4][CH2:5]2

Komponenten

6

Edukt 2

HCID 8028TetrahydrofuranHCID 3229732-Methylene-3-quinuclidone

Produkt 1

HCID 123816982-Methyl-1-azabicyclo(2.2.2)octan-3-oneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

2-Methylenequinuclidin-3-one (17.8 g, 0.13 mol, 1 eq) is dissolved in 40 mL MeOH in a Parr hydrogenation bottle. A THF slurry of 10% Pd/C (0.57 g) is added. The mixture is hydrogenated for 45 min at 45 psi, recharging as needed. The mixture is filtered through a pad of Celite. The Celite is washed with excess MeOH. The solution is concentrated to give a solid and a yellow oil. The mixture is taken up in ether, filtered and concentrated to provide 16.2 g (90%) of 2-methylquinuclidin-3-one. MS (ESI) for C8H13NO m/z 140.2 (M+).

Aufarbeitung

  1. filtrationThe mixture is filtered through a pad of Celite
  2. washThe Celite is washed with excess MeOH
  3. concentrationThe solution is concentrated
  4. customto give a solid
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f8b9486948834d90a0eb4d2c9ca603e2
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176198B2

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