反应详情

温度

-78 °C

To a solution of di-tert-butyl (1S,2R,5R,6R)-2-(tert-butoxycarbonylamino)-3-(dimethylaminomethylene)-4-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylate (15.7 g, 33.8 mmol) in tetrahydrofuran (340 ml) is added triethylamine (6.6 mL, 47.32 mmol). The mixture is cooled to −78° C. Diisobutylaluminium hydride (1N in toluene, 50 mL, 50 mmol) is added over one hour. The mixture is stirred for two additional hours. Then add 30 mL of saturated aqueous ammonium chloride. The mixture is allowed to warm to ambient temperature. The mixture is transferred to a separatory funnel and washed with brine. The organic layer is dried over MgSO4, filtered, and concentrated under reduced pressure to give a residue. The residue is purified by flash chromatography (0 to 50% ethyl acetate/hexanes) to give the title compound (12 g, 33.34 mmol, 83.8% yield). MS (m/z): 422 (M−H).

1. temperatureto warm to ambient temperature
2. customThe mixture is transferred to a separatory funnel
3. washwashed with brine
4. dry with materialThe organic layer is dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customto give a residue
8. customThe residue is purified by flash chromatography (0 to 50% ethyl acetate/hexanes)