HCID 3141336, compound → HCID 10130508, compound

HRID 2303428Notes

Reaction equation

HRID 2303428 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH:6]=[C:7]2[C:12](=[O:13])[CH:11]3[CH2:14][CH2:15][N:8]2[CH2:9][CH2:10]3)=[CH:2]1>CO.[Pd]>[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH:7]2[C:12](=[O:13])[CH:11]3[CH2:10][CH2:9][N:8]2[CH2:15][CH2:14]3)[CH2:2]1

Participants

4

Reactant 1

HCID 3141336HCID 3141336, compound

Product 1

HCID 10130508HCID 10130508, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Quinuclidin-3-one hydrochloride (4.6 g, 28.3 mmol) and powdered anhydrous potassium hydroxide (2.1 g, 37.2 mmol) were dissolved in methanol (25 ml) and stirred for 15 mins. Furan-3-carboxaldehyde (2.83 g, 29.5 mmol) was then added in one portion and the mixture was stirred for an additional 20 hrs. The reaction mixture was then diluted with 40 ml water and cooled to 0° C. yielding 2-((3-furyl)methylene)-1-azabicyclo[2.2.2]octan-3-one as a yellow precipitate, which was collected, washed with distilled water and dried under vacuum (5.16 g, 81.4%). 2-((3-Furyl)methylene)-1-azabicyclo[2.2.2]octan-3-one (2.1 g, 100 mmol) was dissolved in methanol (100 ml) and 10% palladium on charcoal (0.2 g) was carefully added under nitrogen. The suspension was hydrogenated at 50 psig in a Parr hydrogenation apparatus for 8 hrs followed by quenching of the catalyst with a small amount of chloroform. The entire slurry was filtered through a pad of Celite filter aid followed by additional washing of the pad with methanol. Rotary evaporation of the pooled solvents gave the desired product, 2-((3-oxolanyl)methyl)-1-azabicyclo[2.2.2]octan-3-one, as a clear oil that solidified upon cooling (2.05 g, 96.7%).

Workup

  1. customwas collected
  2. washwashed with distilled water
  3. customdried under vacuum (5.16 g, 81.4%)
  4. customby quenching of the catalyst with a small amount of chloroform
  5. filtrationThe entire slurry was filtered through a pad of Celite
  6. filtrationfilter aid
  7. washby additional washing of the pad with methanol
  8. customRotary evaporation of the pooled solvents

Sources & evidence

ORD record
ord-91f71750d26740a49dab72c8429ec8bf
Source dataset
uspto-grants-2002_08
Patent number
US06432975B1

Reaction notes

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