反应详情

In tetrahydrofuran (100 ml), 5-tert-butoxycarbonyl-2-hydroxymethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (2.10 g) was dissolved, followed by the addition of triphenylphosphine (2.66 g) and phthalimide (1.15 g). After the dropwise addition of diethyl azodicarboxylate (1.28 ml), the resulting mixture was stirred at room temperature for 5 hours. After concentration under reduced pressure, the residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=4:1), whereby a colorless solid was obtained. The resulting solid was dissolved in ethanol (40 ml). To the solution, hydrazine hydrate (0.39 ml) was added, followed by heating under reflux for 5 hours. After the solid so precipitated was filtered off, the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (dichloromethane˜dichloromethane:methanol=25:1), whereby the title compound (448 mg, 21%) was obtained.

1. concentrationAfter concentration under reduced pressure
2. customthe residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=4:1), whereby a colorless solid
3. customwas obtained
4. temperatureby heating
5. temperatureunder reflux for 5 hours
6. customAfter the solid so precipitated
7. filtrationwas filtered off
8. concentrationthe filtrate was concentrated under reduced pressure
9. customThe residue was purified by chromatography on a silica gel column (dichloromethane˜dichloromethane:methanol=25:1), whereby the title compound (448 mg, 21%)
10. customwas obtained