反应详情

N-Methyl-4aβ-(3-methoxyphenyl)octahydro-6-oxadecahydroisoquinoline 17 (1.41 g, 4.9 mmol) and hydroxylamine hydrochloride (1.70 g, 24.5 mmol) in EtOH (absolute, 100 mL) were heated to reflux for 5 h. The reaction mixture was allowed to cool to room temperature. Ethanol was removed under reduced pressure. The crude product was taken in to aqueous 2N NaOH solution (100 mL) and extracted with 3:1 CH2Cl2/THF (4×50 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure yielding crude product. The crude product was purified by flash chromatography (neutral alumina, Brockmann activity II-III) eluting with 9:1 ethyl acetate/hexane to afford 1.43 g (96%) of 19 as a white solid (mixture of E/Z): LCMS (ESI): m/z 303.5 (M+H)+.

1. temperatureto reflux for 5 h
2. customEthanol was removed under reduced pressure
3. extractionextracted with 3:1 CH2Cl2/THF (4×50 mL)
4. dry with materialThe combined organic layers were dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customyielding crude product
8. customThe crude product was purified by flash chromatography (neutral alumina, Brockmann activity II-III)
9. washeluting with 9:1 ethyl acetate/hexane