Hydroxyamine hydrochloride → 2-Methyl-1-azabicyclo[2.2.2]octan-3-one oxime

HRID 1018977Notes

Reaction equation

HRID 1018977 reaction equation
Cl.[CH3:2][CH:3]1[C:8](=O)[CH:7]2[CH2:10][CH2:11][N:4]1[CH2:5][CH2:6]2.Cl.[NH2:13][OH:14].O.O.O.C([O-])(=O)C.[Na+]>CCO>[CH3:2][CH:3]1[C:8](=[N:13][OH:14])[CH:7]2[CH2:10][CH2:11][N:4]1[CH2:5][CH2:6]2

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 181803571-Azabicyclo[2.2.2]octan-3-one, 2-methyl-, hydrochlorideHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 858099392-Methyl-1-azabicyclo[2.2.2]octan-3-one oximeYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Methylquinuclidin-3-one hydrochloride from Step L (5.3 g, 30.2 mmol, 1 eq), hydroxylamine hydrochloride (2.5 g, 36.4 mmol, 1.2 eq) and sodium acetate trihydrate (12.4 g, 90.9 mmol, 3 eq) are suspended in 70 mL EtOH and stirred at room temperature. After 24 h, the mixture is concentrated in vacuo. The residue is suspended in CHCl3 and the solids are filtered. The solids are rinsed with excess CH3CN. The combined organic washes are concentrated in vacuo to give 4.65 g (100%) of 2-methyl-1-azabicyclo[2.2.2]octan-3-one oxime. MS (ESI) for C8H14N2O m/z 155.2 (M+H)30 .

Workup

  1. concentrationthe mixture is concentrated in vacuo
  2. filtrationthe solids are filtered
  3. washThe solids are rinsed with excess CH3CN
  4. concentrationThe combined organic washes are concentrated in vacuo

Sources & evidence

ORD record
ord-983c6f58302541e781559f1966ba4519
Source dataset
uspto-grants-2002_11
Patent number
US06486172B2

Reaction notes

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