An Efficient Transformation of Cyclic Ene-carbamates into ω-(N-Formylamino)carboxylic Acids by Ruthenium Tetroxide Oxidation
The ruthenium tetroxide (RuO4) oxidation of cyclic ene-carbamates resulted in the endo-cyclic carbon–carbon double bond cleavage to afford the corresponding ω-(N-formylamino)carboxylic acids in good yields. Substituted cyclic ene-carbamates derived from (3R)-3-hydroxypiperidine hydrochloride were co...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2008/09/01, Vol.56(9), pp.1310-1313 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | Kaname, Mamoru Yoshifuji, Shigeyuki Sashida, Haruki |
| description | The ruthenium tetroxide (RuO4) oxidation of cyclic ene-carbamates resulted in the endo-cyclic carbon–carbon double bond cleavage to afford the corresponding ω-(N-formylamino)carboxylic acids in good yields. Substituted cyclic ene-carbamates derived from (3R)-3-hydroxypiperidine hydrochloride were converted into the N-Boc 4-aminobutyric acids by utilization of the RuO4 oxidation as the key step, which were further transformed into (3R)-4-amino-3-hydroxybutyric acid, an important key intermediate for the synthesis of L-carnitine. |
| doi_str_mv | 10.1248/cpb.56.1310 |
| format | Article |
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Substituted cyclic ene-carbamates derived from (3R)-3-hydroxypiperidine hydrochloride were converted into the N-Boc 4-aminobutyric acids by utilization of the RuO4 oxidation as the key step, which were further transformed into (3R)-4-amino-3-hydroxybutyric acid, an important key intermediate for the synthesis of L-carnitine.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.56.1310</identifier><identifier>PMID: 18758107</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>Carbamates - chemical synthesis ; Carboxylic Acids - chemical synthesis ; Carnitine - chemistry ; Catalysis ; Crystallization ; cyclic ene-carbamate ; Cyclization ; endo-cyclic carbon–carbon double bond cleavage ; gamma-Aminobutyric Acid ; L-carnitine ; Magnetic Resonance Spectroscopy ; Oxidation-Reduction ; RuO4 oxidation ; Ruthenium Compounds - chemistry ; Spectrometry, Mass, Fast Atom Bombardment ; Spectrophotometry, Infrared</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2008/09/01, Vol.56(9), pp.1310-1313</ispartof><rights>2008 The Pharmaceutical Society of Japan</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c447t-a1013fde996fb3635fa7ff2631c00e7d78113bcd0d870026879280257909a72a3</citedby><cites>FETCH-LOGICAL-c447t-a1013fde996fb3635fa7ff2631c00e7d78113bcd0d870026879280257909a72a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18758107$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kaname, Mamoru</creatorcontrib><creatorcontrib>Yoshifuji, Shigeyuki</creatorcontrib><creatorcontrib>Sashida, Haruki</creatorcontrib><title>An Efficient Transformation of Cyclic Ene-carbamates into ω-(N-Formylamino)carboxylic Acids by Ruthenium Tetroxide Oxidation</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>The ruthenium tetroxide (RuO4) oxidation of cyclic ene-carbamates resulted in the endo-cyclic carbon–carbon double bond cleavage to afford the corresponding ω-(N-formylamino)carboxylic acids in good yields. Substituted cyclic ene-carbamates derived from (3R)-3-hydroxypiperidine hydrochloride were converted into the N-Boc 4-aminobutyric acids by utilization of the RuO4 oxidation as the key step, which were further transformed into (3R)-4-amino-3-hydroxybutyric acid, an important key intermediate for the synthesis of L-carnitine.</description><subject>Carbamates - chemical synthesis</subject><subject>Carboxylic Acids - chemical synthesis</subject><subject>Carnitine - chemistry</subject><subject>Catalysis</subject><subject>Crystallization</subject><subject>cyclic ene-carbamate</subject><subject>Cyclization</subject><subject>endo-cyclic carbon–carbon double bond cleavage</subject><subject>gamma-Aminobutyric Acid</subject><subject>L-carnitine</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Oxidation-Reduction</subject><subject>RuO4 oxidation</subject><subject>Ruthenium Compounds - chemistry</subject><subject>Spectrometry, Mass, Fast Atom Bombardment</subject><subject>Spectrophotometry, Infrared</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkEFv1DAQhS0EokvhxB35hEAoWztO4vjGarWlSBWVquVsOc6YukrsxXak5sAP4Nfxl3DYLb3MHN43b_QeQm8pWdOyai_0oVvXzZoySp6hFWUVL-qyZM_RihAiipI17Ay9ivGekLImnL1EZ7TldUsJX6FfG4d3xlhtwSW8D8pF48OokvUOe4O3sx6sxjsHhVahU1mBiK1LHv_5XXz4Vlxmeh7UaJ3_uBD-YV4ONtr2EXczvp3SHTg7jXgPKfgH2wO-yfPfh9fohVFDhDenfY6-X-7226vi-ubL1-3mutBVxVOhKKHM9CBEY7ocpzaKG1M2jGpCgPe8pZR1uid9y3PIpuWibHNYLohQvFTsHL0_-h6C_zlBTHK0UcMwKAd-irIRlWCMVRn8dAR18DEGMPIQ7KjCLCmRS9syty3rRi5tZ_rdyXbqRuif2FO9Gfh8BO5jUj_gP6BCsnqARzNxHIvnk3SnggTH_gJ2Q5Mc</recordid><startdate>20080901</startdate><enddate>20080901</enddate><creator>Kaname, Mamoru</creator><creator>Yoshifuji, Shigeyuki</creator><creator>Sashida, Haruki</creator><general>The Pharmaceutical Society of Japan</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20080901</creationdate><title>An Efficient Transformation of Cyclic Ene-carbamates into ω-(N-Formylamino)carboxylic Acids by Ruthenium Tetroxide Oxidation</title><author>Kaname, Mamoru ; Yoshifuji, Shigeyuki ; Sashida, Haruki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c447t-a1013fde996fb3635fa7ff2631c00e7d78113bcd0d870026879280257909a72a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Carbamates - chemical synthesis</topic><topic>Carboxylic Acids - chemical synthesis</topic><topic>Carnitine - chemistry</topic><topic>Catalysis</topic><topic>Crystallization</topic><topic>cyclic ene-carbamate</topic><topic>Cyclization</topic><topic>endo-cyclic carbon–carbon double bond cleavage</topic><topic>gamma-Aminobutyric Acid</topic><topic>L-carnitine</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Oxidation-Reduction</topic><topic>RuO4 oxidation</topic><topic>Ruthenium Compounds - chemistry</topic><topic>Spectrometry, Mass, Fast Atom Bombardment</topic><topic>Spectrophotometry, Infrared</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kaname, Mamoru</creatorcontrib><creatorcontrib>Yoshifuji, Shigeyuki</creatorcontrib><creatorcontrib>Sashida, Haruki</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kaname, Mamoru</au><au>Yoshifuji, Shigeyuki</au><au>Sashida, Haruki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An Efficient Transformation of Cyclic Ene-carbamates into ω-(N-Formylamino)carboxylic Acids by Ruthenium Tetroxide Oxidation</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2008-09-01</date><risdate>2008</risdate><volume>56</volume><issue>9</issue><spage>1310</spage><epage>1313</epage><pages>1310-1313</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>The ruthenium tetroxide (RuO4) oxidation of cyclic ene-carbamates resulted in the endo-cyclic carbon–carbon double bond cleavage to afford the corresponding ω-(N-formylamino)carboxylic acids in good yields. Substituted cyclic ene-carbamates derived from (3R)-3-hydroxypiperidine hydrochloride were converted into the N-Boc 4-aminobutyric acids by utilization of the RuO4 oxidation as the key step, which were further transformed into (3R)-4-amino-3-hydroxybutyric acid, an important key intermediate for the synthesis of L-carnitine.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>18758107</pmid><doi>10.1248/cpb.56.1310</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Chemical and Pharmaceutical Bulletin, 2008/09/01, Vol.56(9), pp.1310-1313 |
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| language | eng |
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| source | J-STAGE Free; MEDLINE; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | Carbamates - chemical synthesis Carboxylic Acids - chemical synthesis Carnitine - chemistry Catalysis Crystallization cyclic ene-carbamate Cyclization endo-cyclic carbon–carbon double bond cleavage gamma-Aminobutyric Acid L-carnitine Magnetic Resonance Spectroscopy Oxidation-Reduction RuO4 oxidation Ruthenium Compounds - chemistry Spectrometry, Mass, Fast Atom Bombardment Spectrophotometry, Infrared |
| title | An Efficient Transformation of Cyclic Ene-carbamates into ω-(N-Formylamino)carboxylic Acids by Ruthenium Tetroxide Oxidation |
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