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KMID : 0043319940170030204
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Archives of Pharmacal Research
1994 Volume.17 No. 3 p.204 ~ p.206
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An efficient Procedure for the Regioselective Synthesis of 10-Methoxy-11-Hydroxyaporphine from (R,S)-10,11-Dihydroxyaporphine
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Kim Jack C.
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Abstract
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A regioselective perparation of 10-methoxy-11-hydroxyaporphine ("Apocodeine, 1b") form (R, S)-10, 11-dihydroxyaporphine(apomorphine, 1a) is described. The isopropylidene ketal ring of 10, 11-(isopropylidenyldioxy) aporphine (2) obtained by the isopropylidenation of apomorphine, was regioselectively opened by the ten equivalent of timethylaluminum to give 100-hydroxy-11-t-butyloxyaporphine (3). The free 10-hydroxyl position of 3 was methylated with methyl p-toluenesulfonate/NaH, and afforded 10-methoxy-11-t-butyloxyaporphine (4) in high yield. Selective debutylation gave the desired 10-methoxy-11-hydroxyaporphine("apocodeine", 1b) in good yield.
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KEYWORD
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Regiose synthesis, Apocodeine, Apomophine, lsopropylidenation, 10, 11aporphine, 10, -hydroxy-11t-tbutyloxy aporphine, 10-metoxy -11, t-tbuty-loxyaporphine, Trimethylaluminum nucleophile, ring opening
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