Triethylamine → 6,9-Dihydro-5H-6,9-methanocyclohepta[b]pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(cyclopent-3-en-1-ylmethyl)-1,2-dihydropyridin-2-yl trifluoromethanesulfonate (Preparation 26, 3.1 g, 10.1 mmol) in dimethylformamide (20 ml) stirred under nitrogen was added 1,3-bis(diphenylphosphino)propane (0.334 g, 0.8 mmol), triethylamine (1.52 g, 16.6 mmol) and palladium (II) acetate (0.072 g, 0.32 mmol). The reaction mixture was warmed to 100° C. and stirred for 18 h. Triethylamine (1 ml) was added and the reaction mixture was warmed to 110° C. for a further 6 h. The reaction mixture was cooled and poured into saturated brine solution (50%, 75 ml), and the product was extracted with ethyl acetate (4×30 ml). The combined organic extracts were washed with water (2 times), sodium hydrogen carbonate solution and brine before drying (Na2SO4) and concentrating in vacuo. The crude oil was purified by flash chromatography eluting with ethyl acetate:hexane (15:85) to give a colourless oil (1.07 g, 77%).

Provenance & Evidence