Trifluoromethanesulfonic acid, lithium salt → HCID 15252130, compound

Lithium triflate (9.54 g, 61.2 mmol) in acetonitrile (40 cm3) was added dropwise to a stirred solution of 1-methyl-4-aza-1-azoniabicyclo[2,2,2]octane tosylate (18.23 g, 61.2 mmol) in acetonitrile (125 cm3) under an atmosphere of dry nitrogen at room temperature and the mixture left stirring overnight. A white precipitate which had formed was recovered by filtration and washed with dry acetonitrile. Rotary evaporation of the combined filtrate and washings under reduced pressure gave slightly impure (by nmr analysis) 1-methyl-4-aza-1-azoniabicyclo[2,2,2]octane triflate (11.92 g). Continuous extraction (Soxhlet) of the precipitate with dry acetonitrile, followed by evaporation of the extraction solution gave a further 3.34 g of said triflate (total yield 15.26 g, 55.3 mmol, 90%). Lithium tosylate (10.0g, 56.2 mmol, 91.5%) was recovered from the thimble. 1-Methyl-4-aza-1-azoniabicyclo [2,2,2]octane triflate was recrystallised from ethanol-diethyl ether to give analytically pure material (Found: C, 34.9; H, 5.6; F, 20.6; N, 9.8%. Calc. C, 34.8; H, 5.4; F. 20.6; N, 10.1%), m.p. 214°-217° C. (dec ), δH (200 MHz ; D2O soln., ext. TMS ref) 3.05 (s; CH3N+), 3.20 (m; 3×CH2), 3.38(m; 3×CH2) p.p.m. [residual H in D2O, 4.73 (s) p.p.m.], δF (same soln.; ext. CF3CO2H ref.) 0.5 p.p.m. (s; CF3SO3-).