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

HRID 2297647Notes

Reaction equation

HRID 2297647 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 mrol, 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)+.

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-45b66e3449054ae9bd220a3fa18f7246
Source dataset
uspto-grants-2002_12
Patent number
US06492386B2

Reaction notes

Loading…