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

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 regiosel...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2018-12, Vol.50 (23), p.4683-4689
Main Authors: McKinnie, Ryan J., Darweesh, Tasneam, Zito, Phoebe A., Shields, Terrell J., Trudell, Mark L.
Format: Article
Language:English
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Summary: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0037-1609914