An efficient Procedure for the Regioselective Synthesis of 10-Methoxy-11-Hydroxyaporphine from (R,S)-10,11-Dihydroxyaporphine

An efficient Procedure for the Regioselective Synthesis of 10-Methoxy-11-Hydroxyaporphine from (R,S)-10,11-Dihydroxyaporphine

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 regiose...

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Veröffentlicht in:Archives of pharmacal research 1994, Vol.17 (3), p.204-206
1. Verfasser: Kim, Jack C
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description 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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title An efficient Procedure for the Regioselective Synthesis of 10-Methoxy-11-Hydroxyaporphine from (R,S)-10,11-Dihydroxyaporphine
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