2-Cyclohexen-1-one → Rac-6-chloro-3-(3-chloro-benzyl)-3-(3-oxo-cyclohexyl)-1,3-dihydro-indol-2-one

Participants

Reaction Conditions

Reaction Steps

A mixture of rac-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (0.125 g, 0.49 mmol) (from Example 30b supra), 2-cyclohexen-1-one (0.047 g, 0.49 mmol) (Aldrich), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.37 g, 2.4 mmol) (Fluka AG) in methanol (20 mL) was heated at 60° C. for 2 hours. After cooling, the mixture was concentrated, diluted with water, extracted with ethyl acetate (2×100 mL). The organic layers were separated, washed with water and brine. Aqueous layers were back washed with ethyl acetate. The organic layers were combined, dried over Na2SO4 and concentrated. The residue was purified by chromatography (ethyl acetate-hexanes, 2:3, V/V) to give rac-6-chloro-3-(3-chloro-benzyl)-3-(3-oxo-cyclohexyl)-1,3-dihydro-indol-2-one as a white solid. (Yield 0.057 g, 30%).

Provenance & Evidence