An efficient procedure for the regioselective synthesis of 10-methoxy-11-hydroxyaporphine from (R,S)-10,11-dihydroxyaporphine |
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Authors: | Jack C Kim |
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Institution: | 1. Department of Chemistry, Pusan National University, 609-735, Pusan, Korea
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Abstract: | A regioselective preparation of 10-methoxy-11-hydroxyaporphine (“Apocodeine,1b”) from (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 trimethylaluminum
to give 10-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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Keywords: | Regioselective synthesis Apocodeine Apomorphine Isopropylidenation 10 11-(isopropylidenyldioxy)aporphine 10-hydroxy-11-t-butyloxy aporphine 10-methoxy-11-t-butyloxyaporphine Trimethylaluminum nucleophile ring opening |
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