反应详情

Androst-4-ene-3,17-dione is oxidized into 5-oxo-4-nor-3,5-seco-androstane-5,17-dione as in Example 16A (seco-acid). The seco-acid (9.000 g, 31.423 mmol) is slurried with methylammonium chloride (19.5000 g, 288.80 mmol) into acetic acid (75 mL) and heated to reflux under an inert atmosphere. After 3 days, the reaction mixture is allowed to cool to room temperature and diluted with ethyl acetate (EtOAc, 500 mL). The organic solution is washed with water (3×200 mL), saturated aqueous NaHCO3 (2×200 mL) and brine (200 mL), then dried over magnesium sulfate (MgSO4), filtered, concentrated and purified by flash chromatography (1:1:2 EtOAc/CH2Cl2) to afford 4-methyl-4-aza-androst-5-ene-3,17-dione (aza-dione).

1. temperatureheated
2. temperatureto reflux under an inert atmosphere
3. washThe organic solution is washed with water (3×200 mL), saturated aqueous NaHCO3 (2×200 mL) and brine (200 mL)
4. dry with materialdried over magnesium sulfate (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated
7. custompurified by flash chromatography (1:1:2 EtOAc/CH2Cl2)