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

Temperature

100 °C

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%).

1. temperaturethe reaction mixture was warmed to 110° C. for a further 6 h
2. temperatureThe reaction mixture was cooled
3. extractionthe product was extracted with ethyl acetate (4×30 ml)
4. washThe combined organic extracts were washed with water (2 times), sodium hydrogen carbonate solution and brine
5. dry with materialbefore drying (Na2SO4)
6. concentrationconcentrating in vacuo
7. customThe crude oil was purified by flash chromatography
8. washeluting with ethyl acetate:hexane (15:85)

ORD record

ord-1afa62e510c64945baf13245d95eb79c

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07494992B2