New synthetic route to 2,2,6,6-tetraethylpiperidin-4-one: A key-intermediate towards tetraethyl nitroxides
[Display omitted] •Most tetraethyl aminoxyl radicals are made from 2,2,6,6-tetraethylpiperidin-4-one.•Herein, a new synthetic route to 2,2,6,6-tetraethylpiperidin-4-one was designed.•We deliberately avoided unreliable reactions and pressure reactors.•The late introduction of the nitrogen should prov...
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| Veröffentlicht in: | Tetrahedron letters 2019-10, Vol.60 (44), p.151207, Article 151207 |
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| creator | Babić, Nikola Peyrot, Fabienne |
| description | [Display omitted]
•Most tetraethyl aminoxyl radicals are made from 2,2,6,6-tetraethylpiperidin-4-one.•Herein, a new synthetic route to 2,2,6,6-tetraethylpiperidin-4-one was designed.•We deliberately avoided unreliable reactions and pressure reactors.•The late introduction of the nitrogen should provide cheaper 15N-labelled probes.
A new synthetic route to 2,2,6,6-tetraethylpiperidin-4-one and derived aminoxyl (nitroxide) radicals is described. In this preliminary work, 2,2,6,6-tetraethylpiperidin-4-one was obtained from ethyl acetoacetate in 3% yield over eight steps, relying only on common reagents and laboratory equipment for organic synthesis. |
| doi_str_mv | 10.1016/j.tetlet.2019.151207 |
| format | Article |
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•Most tetraethyl aminoxyl radicals are made from 2,2,6,6-tetraethylpiperidin-4-one.•Herein, a new synthetic route to 2,2,6,6-tetraethylpiperidin-4-one was designed.•We deliberately avoided unreliable reactions and pressure reactors.•The late introduction of the nitrogen should provide cheaper 15N-labelled probes.
A new synthetic route to 2,2,6,6-tetraethylpiperidin-4-one and derived aminoxyl (nitroxide) radicals is described. In this preliminary work, 2,2,6,6-tetraethylpiperidin-4-one was obtained from ethyl acetoacetate in 3% yield over eight steps, relying only on common reagents and laboratory equipment for organic synthesis.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2019.151207</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>Aminoxyl radical ; Chemical Sciences ; EPR ; Organic chemistry ; Spin probe ; Synthesis</subject><ispartof>Tetrahedron letters, 2019-10, Vol.60 (44), p.151207, Article 151207</ispartof><rights>2019 Elsevier Ltd</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c386t-9435a3086f29289bc6b646865d640d4f76dc6ed370b04243ce09e97e4ca6f8a83</citedby><cites>FETCH-LOGICAL-c386t-9435a3086f29289bc6b646865d640d4f76dc6ed370b04243ce09e97e4ca6f8a83</cites><orcidid>0000-0002-2481-0564</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.tetlet.2019.151207$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,780,784,885,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://hal.science/hal-02491069$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Babić, Nikola</creatorcontrib><creatorcontrib>Peyrot, Fabienne</creatorcontrib><title>New synthetic route to 2,2,6,6-tetraethylpiperidin-4-one: A key-intermediate towards tetraethyl nitroxides</title><title>Tetrahedron letters</title><description>[Display omitted]
•Most tetraethyl aminoxyl radicals are made from 2,2,6,6-tetraethylpiperidin-4-one.•Herein, a new synthetic route to 2,2,6,6-tetraethylpiperidin-4-one was designed.•We deliberately avoided unreliable reactions and pressure reactors.•The late introduction of the nitrogen should provide cheaper 15N-labelled probes.
A new synthetic route to 2,2,6,6-tetraethylpiperidin-4-one and derived aminoxyl (nitroxide) radicals is described. In this preliminary work, 2,2,6,6-tetraethylpiperidin-4-one was obtained from ethyl acetoacetate in 3% yield over eight steps, relying only on common reagents and laboratory equipment for organic synthesis.</description><subject>Aminoxyl radical</subject><subject>Chemical Sciences</subject><subject>EPR</subject><subject>Organic chemistry</subject><subject>Spin probe</subject><subject>Synthesis</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9kE1LAzEQhoMoWKv_wMNehaZONmk28SAUUSsUveg5pMksTW13SxI_-u_duqI35zIwvM8L8xByzmDMgMnL1ThjXmMel8D0mE1YCdUBGTBVcconih2SAYAAKoDrY3KS0gq6kQoGZPWIH0XaNXmJObgitm8Zi9wW5agcyZGkXXG0mJe79TZsMQYfGipo2-BVMS1ecUdDkzFu0Af7DX7Y6FPxRxVNyLH9DB7TKTmq7Trh2c8ekpe72-ebGZ0_3T_cTOfUcSUz1YJPLAcl61KXSi-cXEghlZx4KcCLupLeSfS8ggWIUnCHoFFXKJyVtbKKD8lF37u0a7ONYWPjzrQ2mNl0bvY3KIVmIPU767Kiz7rYphSx_gUYmL1bszK9W7N3a3q3HXbdY9j98R4wmuQCNq7TENFl49vwf8EX6bWEOw</recordid><startdate>20191031</startdate><enddate>20191031</enddate><creator>Babić, Nikola</creator><creator>Peyrot, Fabienne</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>AAYXX</scope><scope>CITATION</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0002-2481-0564</orcidid></search><sort><creationdate>20191031</creationdate><title>New synthetic route to 2,2,6,6-tetraethylpiperidin-4-one: A key-intermediate towards tetraethyl nitroxides</title><author>Babić, Nikola ; Peyrot, Fabienne</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c386t-9435a3086f29289bc6b646865d640d4f76dc6ed370b04243ce09e97e4ca6f8a83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Aminoxyl radical</topic><topic>Chemical Sciences</topic><topic>EPR</topic><topic>Organic chemistry</topic><topic>Spin probe</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Babić, Nikola</creatorcontrib><creatorcontrib>Peyrot, Fabienne</creatorcontrib><collection>CrossRef</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Babić, Nikola</au><au>Peyrot, Fabienne</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New synthetic route to 2,2,6,6-tetraethylpiperidin-4-one: A key-intermediate towards tetraethyl nitroxides</atitle><jtitle>Tetrahedron letters</jtitle><date>2019-10-31</date><risdate>2019</risdate><volume>60</volume><issue>44</issue><spage>151207</spage><pages>151207-</pages><artnum>151207</artnum><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>[Display omitted]
•Most tetraethyl aminoxyl radicals are made from 2,2,6,6-tetraethylpiperidin-4-one.•Herein, a new synthetic route to 2,2,6,6-tetraethylpiperidin-4-one was designed.•We deliberately avoided unreliable reactions and pressure reactors.•The late introduction of the nitrogen should provide cheaper 15N-labelled probes.
A new synthetic route to 2,2,6,6-tetraethylpiperidin-4-one and derived aminoxyl (nitroxide) radicals is described. In this preliminary work, 2,2,6,6-tetraethylpiperidin-4-one was obtained from ethyl acetoacetate in 3% yield over eight steps, relying only on common reagents and laboratory equipment for organic synthesis.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tetlet.2019.151207</doi><orcidid>https://orcid.org/0000-0002-2481-0564</orcidid><oa>free_for_read</oa></addata></record> |
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| issn | 0040-4039 1873-3581 |
| language | eng |
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| source | ScienceDirect Journals (5 years ago - present) |
| subjects | Aminoxyl radical Chemical Sciences EPR Organic chemistry Spin probe Synthesis |
| title | New synthetic route to 2,2,6,6-tetraethylpiperidin-4-one: A key-intermediate towards tetraethyl nitroxides |
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