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Preparation of (R)-11-hydroxyaporphine directly from (R)-10,11-dihydroxyaporphine ((R)-apomorphine)

✍ Scribed by Jack C. Kim; Sang-Duk Bae; Ji-A Kim; Soon-Kyu Choi

Publisher: Journal of Heterocyclic Chemistry
Year: 1998
Tongue: English
Weight: 262 KB
Volume: 35
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570350307

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✦ Synopsis

Abstract

A Regioselective synthesis of (R)‐11‐hydroxyaporphine 2 directly from (R)‐10,11‐dihydroxyaporphine ((R)‐apomorphine, 1) is described for the first time. The isopropylidene ketal ring of 10,11‐(isopropyl‐idenyldioxy)aporphine 5 obtained by the isopropylidenation of apomorphine was regioselectively opened by ten equivalents of trimethylaluminum to give (R)‐10‐hydroxy‐11‐tert‐butyloxyaporphine 6. The free 10‐hydioxyl position of 6 was triflated with N‐pbenyltrifluoromethanesulfonimide and potassium carbonate under reflux to give (R)‐10‐[(trifluoromethyl)sulfonyloxy]‐11‐tert‐butyloxyaporphine 7. The reduced product, 11‐tert‐butyloxyaporphine 8 was prepared from 7 by a palladium‐catalyzed hydrogenolysis. The ether cleavage of (R)‐11‐tert‐butyloxyaporphine with 48% hydrobromic acid afforded the desired (R)‐11‐hydroxyaporphine 2 in good yield.

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