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Letter

Synthesis of 2-Fluoro-11-hydroxy-N-propylnoraporphine: A Potential Dopamine D₂ Agonist

Supporting Info

Ao Zhang, Csaba Csutoras,^† Rushi Zong, and John L Neumeyer*

Medicinal Chemistry Laboratory, Alcohol and Drug Abuse Research Center, McLean Hospital, Harvard Medical School, 115 Mill Street, Belmont, Massachusetts 02478

Org. Lett., 2005, 7 (15), pp 3239–3242

DOI: 10.1021/ol051010d

Publication Date (Web): June 18, 2005

†

Current Address: Department of Chemistry, Eszterházy Károly University, 4 Leányka Street, Eger, Hungary, H-3300.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, neumeyer@mclean.harvard.edu

Abstract

2-Fluoro-11-hydroxy-N-propylnoraporphine 4 (2-F-11-OH-NPa) was synthesized from thebaine in 13 steps with an overall yield of 1.35%. The key steps included the Pd-catalyzed 3-dehydroxylation of 14-hydroxymorphine, S_N2 substitution of Ts^- by F^-, and CH₃SO₂OH-promoted rearrangement of the substituted morphinandiene. The dopamine binding affinity of this compound was also investigated on rat brain membranes, and as expected, this compound displayed high affinity and selectivity at the D₂ receptor.

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History

Published In Issue July 21, 2005
Received May 3, 2005

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Letter

Synthesis of 2-Fluoro-11-hydroxy-N-propylnoraporphine: A Potential Dopamine D₂ Agonist