• Archives of Pharmacal Research
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• 제17권3호
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• pp.204-206
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• 1994

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.