反应详情

The O-demethylation procedure described in Steroids 11:151 [1968] was modified for this synthesis. First, 16.1 g (62.3 mmol) of dextrorphan, 2, were dissolved in 500 mL hot acetone, to which 15.5 g (64.4 mmol) AM-ex-OL (Aldrich) and 17.13 g (123.9 mmol) potassium carbonate were added. The reaction mixture was stirred at reflux overnight under an atmosphere of argon. After cooling, the reaction mixture was poured into a separatory funnel to which 500 mL water were added. Extraction with 1×500 and 2×250 mL benzene was followed by washing the combined organics with 1×250 mL water and removing the solvent in vacuo to give 27.51 g (96%) product as a white glass which was homogeneous by TLC. Recrystallization in ethyl acetate gave pure 3 as white crystals, mp 138°-139° C. EIMS m/z 461. Anal. (C31H31N3) C, H, N.

1. customwas modified for this synthesis
2. additionwere added
3. temperatureat reflux overnight under an atmosphere of argon
4. temperatureAfter cooling
5. additionwere added
6. extractionExtraction with 1×500 and 2×250 mL benzene
7. washby washing the combined organics with 1×250 mL water
8. customremoving the solvent in vacuo