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A broadly applicable Diels-Alder based Synthesis of Ketamine related Arylcyclohexylamines

09 November 2022, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Herein we report the synthesis of both aryl derivatives of ketamine and aryl derivatives of ketamine’s major metabolites hydroxynorketamine (HNK), norketamine (NK) and dehydronorketamine (DHNK) via a microwave-assisted Diels-Alder reaction to form the substituted cyclohexane core structure. Starting with aryl acrylic esters as dienophiles and siloxybutadienes as diene counterparts, a wide range of substituted arylcyclohexylamines was obtained after several modification steps of the initial Diels-Alder products.

Keywords

Ketamine
HNK
Diels-Alder

Supplementary materials

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Experimental Procedures and Spectra
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Version History

Nov 09, 2022 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2022-xf1l9
D O I: 10.26434/chemrxiv-2022-xf1l9 [opens in a new tab]

Funding

Ministerium für Kultur und Wissenschaft des Landes Nordrhein-Westfalen
322 – 8.03.04-127491
Bundesministerium für Wissenschaft, Forschung und Wirtschaft
50WB2128

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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