反应详情

A solution of 1,1-dimethylethyl {(1S)-2-(4-bromophenyl)-1-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]ethyl}carbamate (21.7 mmol), 1-ethoxyvinyltri-n-butylin (43.5 mmol), and trans-dichlorobis(triphenylphospine)palladium(II) (5 mol %) were stirred in anhydrous dioxane (300 mL) at 100° C. for 3 h. The reaction was then concentrated in vacuo and redissolved in a solution of tetrahydrofuran and water (3:1, 400 mL). The mixture was treated with N-bromosuccinimide (108.8 mmol) and stirred at RT for half an hour. The reaction solution was then concentrated to dryness and redissolved in ethyl acetate (150 mL). Precipitate formed upon addition of hexanes (350 mL) and was filtered and dried to afford the title product as yellow solid (71%). ESMS [M+H]+: 502.4.

1. concentrationThe reaction was then concentrated in vacuo
2. dissolutionredissolved in a solution of tetrahydrofuran and water (3:1, 400 mL)
3. concentrationThe reaction solution was then concentrated to dryness
4. dissolutionredissolved in ethyl acetate (150 mL)
5. customPrecipitate formed upon addition of hexanes (350 mL)
6. filtrationwas filtered
7. customdried