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

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Reaction Steps

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)+.

Provenance & Evidence