Quinuclidine → 1-(3-Azido-3-methylbutyl)-1-azoniabicyclo[2.2.2]octane methanesulfonate

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Reaction Steps

In a 1 dram vial, a solution of 3-azido-3-methylbutyl methanesulfonate (0.45 g, 2.19 mmol) and quinuclidine (0.21 g, 1.9 mmol) in 2-pentanone (2.0 mL) was heated on a heat block at 110° C. for 16 h. The suspension was cooled, filtered, and rinsed with diethyl ether (50 mL). The filtrate was discarded and the solid was dried under high vacuum to give a white solid. (052 g, 74.7%). 1H NMR (D2O, 400 MHz): δ 1.35 (s, 6H), 1.95-2.05 (m, 8H), 2.18-2.22 (pent, J=3.6, 1H), 2.82 (s, 3H), 3.24-3.30 (m, 2H), 3.38-3.45 (m, 6H). LRMS (ESI+) for C12H23N4+(223.2); Found: 223 (M+).

Provenance & Evidence