1,2-Dimethoxyethane → 1-Azabicyclo(2.2.2)octane-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

3-Quinuclidinone (28.8 g, 0.23 mmol) and tosylmethyl isocyanide (58.4 g, 0.30 mol) were dissolved in 23 ml of absolute ethanol and 800 ml of dimethoxyethane and cooled to 0° C. Potassium t-butoxide (64.4 g, 0.57 mol) was added portionwise, and the reaction continued stirring at 0° C. for 30 minutes, then heated at 40° C. for 30 minutes. The reaction was cooled to room temperature and stirred for 16 hours. The reaction was filtered and the filtrate was concentrated in vacuo to afford a clear, golden brown oil (50 g) which was chromatographed on alumina eluting with ethyl acetate thus affording the title product, 23.3 g (74%).

Provenance & Evidence