反应详情

To a mixture of 2.9 g (4.54 mmol) 4-methoxy-N,14-bis(2,2,2-trichloroethoxycarbonyl)-morphinan-6-one in 130 ml ethanol were added 15 g (280.4 mmol) NH4Cl and this mixture was stirred and refluxed. During 0.5 h 12 g (177 mg) activated zinc powder were added portionwise and the resulting mixture was refluxed for 1 h. After cooling and filtration, the filtrate was evaporated. The residue was dissolved in water, basified with saturated NaHCO3 solution and extracted with CHCl3. The organic layer was washed with brine, dried and evaporated to give an oil which was crystallized with isopropyl ether to yield 690 mg (53%) 14-hydroxy-4-methoxymorphinan-6-one, m.p. 137°-139°, [α]D26 --66.5°. (C 1.08, CHCl3).

1. temperaturerefluxed
2. temperaturethe resulting mixture was refluxed for 1 h
3. temperatureAfter cooling
4. filtrationfiltration
5. customthe filtrate was evaporated
6. dissolutionThe residue was dissolved in water
7. extractionextracted with CHCl3
8. washThe organic layer was washed with brine
9. customdried
10. customevaporated
11. customto give an oil which
12. customwas crystallized with isopropyl ether