Synthesis of the 5-Fluoro-4-hydroxypentyl Side Chain Metabolites of Synthetic Cannabinoids 5F-APINACA and CUMYL-5F-PINACA
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 hy...
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Published in | Synthesis (Stuttgart) Vol. 50; no. 23; pp. 4683 - 4689 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
STUTTGART
Thieme Medical Publishers
01.12.2018
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Subjects | |
Online Access | Get more information |
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Summary: | 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. |
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ISSN: | 0039-7881 1437-210X |
DOI: | 10.1055/s-0037-1609914 |