反应详情

温度

60 °C

To a solution of 1-ethyl 2-tert-butyl 6-cyano-3,4-dihydroisoquinoline-1,2(1H)-dicarboxylate (0.5 g, 1.51 mmol) in acetic acid (5.00 mL) and pyridine (10 mL) was added a mixture of Raney-nickel (0.5 g, 1.51 mmol) and water (5 mL), and then sodium hypophosphite monohydrate (2.5 g, 23.59 mmol) was added thereto under argon atmosphere. The mixture was stirred at 60° C. for 3 hr, and then overnight at 100° C. The reaction mixture was filtered through Celite, and the filtrate was diluted with ethyl acetate. The mixture was washed with aqueous ammonium chloride solution, aqueous sodium hydrogencarbonate solution and brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 5→70% ethyl acetate/hexane) to give 1-ethyl 2-tert-butyl 6-formyl-3,4-dihydroisoquinoline-1,2(1H)-dicarboxylate (0.430 g, 1.290 mmol, 85%) as a colorless oil.

1. customovernight
2. customat 100° C
3. filtrationThe reaction mixture was filtered through Celite
4. additionthe filtrate was diluted with ethyl acetate
5. washThe mixture was washed with aqueous ammonium chloride solution, aqueous sodium hydrogencarbonate solution and brine
6. dry with materialdried over magnesium sulfate
7. customthe solvent was evaporated under reduced pressure
8. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 5→70% ethyl acetate/hexane)