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

HRID 2298380Notes

Reaction equation

HRID 2298380 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.[OH-].[Na+]>CCO.N1C=CC=CC=1>[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

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 181803571-Azabicyclo[2.2.2]octan-3-one, 2-methyl-, hydrochloride

Product 1

HCID 858099392-Methyl-1-azabicyclo[2.2.2]octan-3-one oximeYield 96.4%

Reagents, catalysts & solvents 1

HCID 21975839Pyridine ethanolSolvent

Procedure

The product from Step 158b (3.2 g, 23.0 mmol, 1 eq) and hydroxylamine hydrochloride (1.6 g, 23.0 mmol, 1 eq) are dissolved in 20 mL EtOH/pyridine (4:1) and stirred at room temperature. After 5 days, water and solid NaOH are added to adjust pH to pH 11. The mixture is extracted with several portions of CHCl3. The combined organic layers are dried over MgSO4, filtered and concentrated to give 3.42 g (96%) of 2-methyl-1-azabicyclo[2.2.2]octan-3-one oxime as a 1:2.6 mixture of oxime isomers. Partial 1H NMR (CDCl3, 300 MHz) δ 1.53 ppm (d, 2-CH3, 0.8H), 1.38 (d, 2-CH3, 2.2H). MS (ESI) for C8H14N2O m/z 154.8 (M+H)+.

Workup

  1. extractionThe mixture is extracted with several portions of CHCl3
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-900725a1b1254301961007a735603746
Source dataset
uspto-grants-2002_12
Patent number
US06492385B2

Reaction notes

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