反应详情

To a solution of N-t-butoxycarbonyl-3-pyrroline (69.3 g) and NMO (72.2 g) in tetrahydrofuran (340 mL), t-butanol (210 mL) and water (100 mL) was added OsO4 (2.5% solution in t-butanol, 4.8 mL), the mixture was heated under reflux for 2.5 hours, and then concentrated in vacuo. After dilution of the residue with brine, the mixture was extracted with ethyl acetate. The organic extracts were concentrated in vacuo. Flash chromatography (silica, hexane:ethyl acetate=1:1) of the residue gave

1. temperaturethe mixture was heated
2. temperatureunder reflux for 2.5 hours
3. concentrationconcentrated in vacuo
4. extractionAfter dilution of the residue with brine, the mixture was extracted with ethyl acetate
5. concentrationThe organic extracts were concentrated in vacuo
6. customFlash chromatography (silica, hexane:ethyl acetate=1:1) of the residue gave