Cyclohexene → HCID 19083210, compound

Participants

Reaction Steps

3-(1-Cyclopropylcarbamoyl-2,2-dimethyl-propylcarbamoyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-5-methyl-hexanoic acid-1-benzyl ester (3.46 g, 6.02 mmol) was dissolved in ethyl acetate (90 ml) and cyclohexene (10 ml) and the solution was placed under a blanket of argon. 10% palladium on charcoal catalyst (0.75 g) was added and the mixture was heated at reflux for 4 hours. The mixture was cooled and the catalyst was removed by filtration and the filtrate was evaporated to leave a pale yellow foam. Column chromatography (silica gel, gradient elution, 30 to 60% ethyl acetate in hexane) afforded the desired product as a white solid (1.2 g, 41%). 1H-NMR (CD3OD); δ 8.30 (1H, m), 8.08 (1H, m), 7.81 (5H, m), 7.11 (1H, m), 4.11 (0.75H, m), 3.92 (0.25H, m), 3.76 (1 H, m), 3.13-2.85 (2H, br m), 1.72 (1H, m), 1.53 (2H, m), 1.14 (6.7H, s), 1.08 (2.3H, s) and 0.86 (6H, m).

Provenance & Evidence