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

Participants

Reaction Steps

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)+.

Provenance & Evidence