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

HRID 890942

Reaction equation

HRID 890942 reaction equation
[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

Participants

6

Reactant 2

HCID 8028TetrahydrofuranHCID 3229732-Methylene-3-quinuclidone

Product 1

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

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

2-Methylenequinuclidin-3-one (17.8 g, 0.1296 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+).

Workup

  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

Sources & evidence

ORD record
ord-d078592b39b14c47a1912f2b8c155eea
Source dataset
uspto-grants-2006_02
Patent number
US07001900B2

Linked notes

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