1,2,3,4-Tetrahydroquinoline → 8-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)-8-azabicyclo[3.2.1]oct-2-ene-3-yl trifluoromethanesulfonate

Participants

Reaction Steps

1.13 g of 1,2,3,4-tetrahydroquinoline, 85 ml of dichloromethane and 1.54 ml of triethylamine are placed in a 250 ml three-necked flask under a nitrogen atmosphere. 0.834 g of triphosgene is added at 0° C., and the reaction is then left to stir at ambient temperature for 4 h. 2.27 g of 8-azabicyclo[3.2.1]oct-2-ene-3-yl trifluoromethylsulfonate hydrochloride and 1.19 ml of triethylamine are subsequently added and the reaction mixture is then refluxed for 18 h. 200 ml of a saturated aqueous solution of sodium hydrogen carbonate are added and the aqueous phase is extracted three times with dichloromethane. The organic phases are combined, dried over sodium sulfate and evaporated under reduced pressure. The residue is chromatographed on silica gel with an 8/2 mixture of heptane/ethyl acetate. 3.21 g of 8-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)-8-azabicyclo[3.2.1]oct-2-ene-3-yl trifluoromethanesulfonate are obtained.

Provenance & Evidence