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Synthesis 2007(24): 3787-3790  
DOI: 10.1055/s-2007-990902
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© Georg Thieme Verlag Stuttgart · New York

Facile Synthesis of 11-Hydroxy-2-methoxyaporphine: A Potential Dopamine D1 Receptor Ligand

Yu-Gui Si, John L. Neumeyer
Alcohol and Drug Abuse Research Center, McLean Hospital, Harvard Medical School, 115 Mill Street, Belmont, MA 02478, USA
Fax: +1(617)8552519; e-Mail: jneumeyer@mclean.harvard.edu;
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Publication History

Received 24 May 2007
Publication Date:
15 November 2007 (online)

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Abstract

11-Hydroxy-2-methoxyaporphine was synthesized from oripavine in three steps with an overall yield of 37.8%. The key step involved the palladium on carbon catalyzed reduction of 11-hydroxy-2-methoxy-10-O-[(trifluoromethyl)sulfonyl]aporphine using magnesium metal in methanol at room temperature in the presence of ammonium acetate.

Key words

aporphine - synthesis - rearrangement - reduction - de­oxy­genation