1-Azabicyclo(2.2.2)octan-3-one, hydrochloride (1:1) → 3-Quinuclidinone

HRID 1987852Notes

Reaction equation

HRID 1987852 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4](=[O:10])[CH2:3]2.C[O-].[Na+]>CO>[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4](=[O:10])[CH2:3]2

Participants

4

Reactant 2

HCID 1020191-Azabicyclo(2.2.2)octan-3-one, hydrochloride (1:1)HCID 10942334Sodium Methoxide

Product 1

HCID 195073-Quinuclidinone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

100 g (0.62 mol) of quinuclidin-3-one hydrochloride are suspended in 21 of methanol. At 0° C., a solution of 33.4 g (0.62 mol) of sodium methoxide in 250 ml of methanol is slowly added dropwise. The mixture is stirred at room temperature for 16 h. The resulting precipitate is filtered off with suction, and the filtrate is concentrated in vacuo. The residue is partitioned between chloroform and water and extracted with chloroform the combined organic phases are dried over sodium sulfate and concentrated in vacuo. 58.8 g (75.9% of theory) of the title compound are obtained.

Workup

  1. filtrationThe resulting precipitate is filtered off with suction
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe residue is partitioned between chloroform and water
  4. extractionextracted with chloroform the combined organic phases
  5. dry with materialare dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8af44fd5393a4dfb910f6e74dde9a97d
Source dataset
uspto-grants-2009_06
Patent number
US07553851B2

Reaction notes

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