反应详情

2-(cyclohexylmethoxy)-1H-isoindole-1,3(2H)-dione (11.8 mmol, 3.05 g) was combined with hydrazine (12.9 mmol, 0.41 mL) in anhydrous THF (25 mL) under nitrogen. The reaction immediately formed a white suspension and was allowed to stir at room temperature for 48 hours. The suspension was filtered directly into a flask containing 4-methoxybenzenesulfonyl chloride (9.5 mmol, 1.97 g) and diisopropylethylamine (11.6 mmol, 2.03 mL) was added. After stirring at room temperature for 18 hours, the reaction was concentrated to a solid residue and partitioned between ethyl acetate and 1N HCl. The organic layer was separated and washed with a saturated aqueous solution of sodium bicarbonate, and brine, and dried over magnesium sulfate. The product was concentrated to a solid and purified by silica gel chromatography (2:1 hexanes/ethyl acetate) providing 2.55g (80%) of a yellow solid. H1-NMR (CDCl3): δ 7.81 (2H,d), 6.97 (2H,d), 6.78 (1H,s), 3.85 (3H,s), 3.75 (2H,d), 1.65-1.55 (6H,m), 1.25-1.07 (3H,m), 0.93-0.85 (2H,m).

1. customThe reaction
2. customimmediately formed a white suspension
3. filtrationThe suspension was filtered directly into a flask
4. additionwas added
5. stirringAfter stirring at room temperature for 18 hours
6. concentrationthe reaction was concentrated to a solid residue
7. custompartitioned between ethyl acetate and 1N HCl
8. customThe organic layer was separated
9. washwashed with a saturated aqueous solution of sodium bicarbonate, and brine
10. dry with materialdried over magnesium sulfate
11. concentrationThe product was concentrated to a solid
12. custompurified by silica gel chromatography (2:1 hexanes/ethyl acetate)