Triethylamine → 1-Benzyl-4-(4-fluorophenyl)-l-azoniabicyclo[3.1.1]hept-3-ene trifluoromethanesulphonate

Participants

Reaction Steps

Triethylamine (1.5 ml) was added to a solution of (+)-1-benzyl-3-hydroxymethyl-4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine (2.82 g) in toluene (22.18 g) and the mixture was stirred at ambient temperature. The solution was cooled to 5° C. in an ice/water bath and the trifluoromethanesulphonic anhydride (1.8 ml) was added dropwise over 5 minutes. The mixture was stirred at 0° C. to room temperature for 4 hours, then stood for 48 hours. Water (25 ml) was added. The mixture was stirred for 2 minutes and then ethyl acetate and 4M-NaOH were added to dissolve an insoluble oil. The organic layer was separated, washed with water (25 ml), and then dried, filtered and evaporated to give 1-benzyl-4-(4-fluorophenyl)-1-azoniabicyclo[3.1.1]hept-3-ene trifluoro-methanesulphonate as an oil The oil was triturated with 60-80° C. petrol to give a solid.

Provenance & Evidence