反应详情

Tert-butyl[(1S,5R,6R)-6-(nitromethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetate (peak 1, 21.6 g, 80.8 mmol) was dissolved in ethanol (200 mL) and water (100 mL). To the solution, iron powder (45.1 g, 80.8 mmol) and ammonium chloride (2.59 g, 48.5 mmol) were added, and the mixture was stirred for 5.5 hours under heating to reflux. To the reaction solution, iron powder (9.0 g, 161 mmol) was then further added, and the mixture was further stirred for 2 hours under heating to reflux. The mixture was allowed to cool, then diluted with a saturated aqueous solution of sodium bicarbonate and ethyl acetate, and filtered to remove insoluble matter. From the filtrate, the organic solvent was distilled off under reduced pressure, followed by extraction with ethyl acetate from the aqueous layer. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was purified by amino column chromatography to obtain the compound of interest as a pale yellow oil (5.5 g).

1. temperatureunder heating to reflux
2. stirringthe mixture was further stirred for 2 hours
3. temperatureunder heating to reflux
4. temperatureto cool
5. filtrationfiltered
6. customto remove insoluble matter
7. distillationFrom the filtrate, the organic solvent was distilled off under reduced pressure
8. extractionfollowed by extraction with ethyl acetate from the aqueous layer
9. washThe organic layer was washed with saturated saline
10. dry with materialdried over anhydrous magnesium sulfate
11. distillationThen, the solvent was distilled off under reduced pressure
12. customthe residue was purified by amino column chromatography