反应详情

To a solution of 8-amino-2,3,8,9-tetrahydropyrano[3,2-e]isoindol-1(7H)-one (1) (200 mg, 0.98 mmol) in anhydrous MeOH (20 ml) was added 3-(5-fluoro-1H-indol-3-yl) propanal (2) (191 mg, 1 mmol), AcOH (0.14 ml), and NaBH3CN (123 mg, 1.96 mmol). Resulting reaction mixture was stirred at room temperature for 2 hr. The solvent was removed in vacuo and the residue was re-dissolved in CH2Cl2 (150 ml). The solution was washed with 1 N NaOH (20 ml) and H2O, Sat. NaCl. The organic solution was separated, dried over Na2SO4, then concentrated in vacuo. The crude compound was purified on silica gel eluting with EtOAc/Hexane (4:1) to yield (3) (304 mg, 82%) as a white solid. MS (APPI) m/z 380.

1. customResulting
2. customreaction mixture
3. customThe solvent was removed in vacuo
4. dissolutionthe residue was re-dissolved in CH2Cl2 (150 ml)
5. washThe solution was washed with 1 N NaOH (20 ml) and H2O, Sat. NaCl
6. customThe organic solution was separated
7. dry with materialdried over Na2SO4
8. concentrationconcentrated in vacuo
9. customThe crude compound was purified on silica gel eluting with EtOAc/Hexane (4:1)