A flow electrochemistry‐enabled synthesis of 2‐substituted N ‐(methyl‐ d )piperidines

Autor:	Azzam A. M. AL‐Hadedi, Stuart Sawyer, Stuart J. Elliott, Robert A. Green, Daniel J. O'Leary, Richard C. D. Brown, Lynda J. Brown
Rok vydání:	2022
Předmět:	Organic Chemistry Drug Discovery Radiology Nuclear Medicine and imaging Biochemistry Spectroscopy Analytical Chemistry
Zdroj:	Journal of Labelled Compounds and Radiopharmaceuticals. 65:361-368
ISSN:	1099-1344 0362-4803
DOI:	10.1002/jlcr.4006
Popis:	A synthesis of N-monodeuteriomethyl-2-substituted piperidines is described. An efficient and readily scalable anodic methoxylation of N-formylpiperidine in an undivided microfluidic electrolysis cell delivers methoxylated piperidine 3, which is a precursor to a N-formyliminium ion and enables C-nucleophiles to be introduced at the 2-position. The isotopically labelled N-deuteriomethyl group is installed using the Eschweiler-Clarke reaction with formic acid-d2 and unlabelled formaldehyde. Monodeuterated N-methyl groups in these molecular systems possess small isotropic proton chemical shift differences important in the investigation of molecules that are able to support long-lived nuclear spin states in solution nuclear magnetic resonance.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::7fac8afd278e5ead9d112fe6e2669d47 https://doi.org/10.1002/jlcr.4006 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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