Cyclopentane, methylene- → HCID 70495943, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution 4-{[1-(3-bromo-phenyl)-meth-(E)-ylidene]amino}-benzoic acid methyl ester (3.2 g, 10.0 mmol) in acetonitrile (16.0 mL) were added methylene-cyclopentane (4.0 mL, 40.0 mol) and scandium(III) trifluoromethanesulfonate (Sc(OTf)3) (980.0 mg, 2.0 mmol). The resulting mixture solution was stirred at 80° C. for 16 h in sealed tube. The mixture solution was diluted with ethyl acetate (300 mL) and washed with water (100 mL×2) and brine (100 mL×2) and then dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by ISCO combi-flash chromatography (gradient elution, 10-50% ethyl acetate in petroleum ether) to afford 2′-(3-bromo-phenyl)-2′,3′-dihydro-1′H-spiro[cyclopentane-1,4′-quinoline]-6′-carboxylic acid methyl ester (1.6 g, 40%) as a light yellow solid: MS (ESI) M+1=400.0.

Provenance & Evidence