Acetic Acid → HCID 19610953, compound

Participants

Reaction Conditions

Reaction Steps

Tertiary butyllithium in pentane (7 ml of a 1.7 molar solution, 0.0104 mole) in dry pentane (25 ml) at -65° C. under nitrogen was treated with 3-(tetrazol-2-yl)-1-azabicyclo[2.2.2]octane (the free base of E15) (1.0 g; 5.2 mmole) in a dry pentane (50 ml)/dry THF (10 ml) mixture, maintaining an internal temperature of -65° C. Stirring was continued for 10 minutes. Bromine (2 eq, 1.66 g, 10.4 mmole) in dry pentane (5 ml) was then added dropwise. The mixture was then immediately quenched with glacial acetic acid (2 eq, 0.62 ml, 10.4 mmole), then partitoned between aqueous potassium carbonate (20 ml) and chloroform (5×20 ml). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo, to afford an oil which was chromatographed on neutral alumina eluting with ethyl acetate, to afford in order of elution the title compound (free base) (220 mg as an oil) and unreacted starting material. The free base was converted to the oxalate salt and recrystallised from acetone/ether to give the title compound (E40) as a white crystalline solid (0.113 g, 0.00032 mole, 6%) m.p. 165° C. (decomp.).

Provenance & Evidence