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During the course of this work, selective demethylation of 10,11-dimethoxyaporphine(14) was studied in order to prepare 15,s an isomer of apocodeine (16). Reaction of 14 with the sodium salt of ethanethiol in DMF at loo" gave a 65% yield of apocodeine (16). None of the isomeric mono-ether 15 could be detected in the crude reaction mixture. Surprisingly, use of the more sterically hindered reagents, sodium thioisopropoxide and sodium thio-tert -butoxide, also gave only apocodeine, again in good yield. Although small amounts of the bis dealkylation product, apomor-phine (l),were observed in the reactions involving sodium thioethoxide and sodium thioisopropoxide, no apomor-phine was detected in the sodium thio-tert-butoxide reac-tion. Reaction of 14 with 20% hydrochloric acid at 120" also gave only apocodeine (16) as the monodemethylation product, but in lower yield, 35%.

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