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Synthesis 2018; 50(23): 4683-4689
DOI: 10.1055/s-0037-1609914
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© Georg Thieme Verlag Stuttgart · New York

Synthesis of the 5-Fluoro-4-hydroxypentyl Side Chain Metabolites of Synthetic Cannabinoids 5F-APINACA and CUMYL-5F-PINACA

Ryan J. McKinnie
Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA   Email: mtrudell@uno.edu
,
Tasneam Darweesh
Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA   Email: mtrudell@uno.edu
,
Phoebe A. Zito
Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA   Email: mtrudell@uno.edu
,
Terrell J. Shields Jr.
Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA   Email: mtrudell@uno.edu
,
Mark L. Trudell*
Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA   Email: mtrudell@uno.edu
› Author Affiliations
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Publication History

Received: 15 June 2018

Accepted after revision: 18 July 2018

Publication Date:
14 August 2018 (online)

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Abstract

An efficient method for the construction of the 5-fluoro-4-hydroxypentyl side chain common to a number of synthetic cannabinoid metabolites was developed. A series of hydroxyl protecting groups was examined to assess the viability as orthogonal protecting groups for epoxidation and regioselective hydrofluorination. The 1-[5-fluoro-4-(diphenyl-tert-butylsilyloxy)]pentyl tosylate was prepared in 67% overall yield (six steps) from pent-4-en-1-ol and was employed for the synthesis of the 4-hydroxy metabolites of the synthetic cannabinoid 5F-APINACA and CUMYL-5F-PINACA.

Key Words

cannabinoid - metabolite - hydrofluorination - epoxidation - 5F-APINACA - CUMYL-5F-PINACA

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609914.
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