Reacción #607976

Ecuación de reacción

(3aR,6aR)-1-(5-iodopyridin-2-yl)hexahydro-cyclopenta[b]pyrrol-2(1H)-one

Ethynylbenzene

triethylamine

→

title compound

Rendimiento 96.4%

(−)-(3aR,6aR)-1-(5-(phenylethynyl)pyridin-2-yl)hexahydrocyclopenta[b]pyrrol-2(1H)-one

Rendimiento 96.4%

Disolventes

THF

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroArgon was bubbled through the solution
2. 2
   Filtraciónthe solids were filtered off
3. 3
   Lavadowashed with ethyl acetate
4. 4
   ConcentraciónThe filtrate was concentrated in vaccuo
5. 5
   Otrothe residue was purified by flash chromatography (SiO2, 20 g)

Procedimiento

In a 10 ml Pyrex tube were dissolved (3aR,6aR)-1-(5-iodopyridin-2-yl)hexahydro-cyclopenta[b]pyrrol-2(1H)-one (107 mg, 326 μmol) in 2 ml of THF. Argon was bubbled through the solution. Ethynylbenzene (59.9 mg, 64.5 μl, 587 μmol, 1.8 equiv.), triethylamine (99.0 mg, 136 μmol, 978 μmol, 3.0 equiv.), bis(triphenylphosphine)palladium(II) chloride (13.7 mg, 19.6 μmol, 0.06 equiv.), triphenylphosphine (1.71 mg, 6.52 μmol, 0.02 equiv.), and copper (I) iodide (1.86 mg, 9.78 μmol, 0.03 equiv.) were added. The dark brown solution was stirred at 50° C. for 2 h. The residue was taken up in ethyl acetate, the solids were filtered off and washed with ethyl acetate. The filtrate was concentrated in vaccuo and the residue was purified by flash chromatography (SiO2, 20 g) using a 0% to 60% ethyl acetate in heptane gradient. One obtained 95 mg (96%) of the title compound as a viscous yellow oil, MS: m/e=303.2 (M+H+).

Fuente