1-Azabicyclo[2.2.2]octane-4-carbonitrile → Quinuclidin-4-ylmethanamine

Participants

Reaction Conditions

Reaction Steps

A solution of 4-cyanoquinuclidine (0.30 g, 2.2 mmol) in diethyl ether (5 mL) was slowly added to a suspension of LAH (0.167 g, 4.41 mmol) in diethyl ether (15 mL) at 0° C. The reaction was stirred at 23° C. for 3 h, then quenched with sodium sulfate decahydrate and stirred for 30 more minutes. Ethyl acetate was then added and, after 30 minutes, celite was added and the suspension was filtered on celite. The filtrate was concentrated to dryness to give an oil (0.310 g, quant.). The compound was used as such for the next reaction. 1H NMR (400 MHz, CDCl3) δ ppm: 1.31-1.40 (6H, m), 2.43 (2H, s), 2.86-2.94 (6H, m).

Provenance & Evidence