{"title":"异烟酸乙酯自由基氨基化法合成NMDA拮抗剂CGS 19755。","authors":"I Martin, J Anvelt, L Vares, I Kühn, A Claesson","doi":"10.3891/acta.chem.scand.49-0230","DOIUrl":null,"url":null,"abstract":"<p><p>The NMDA antagonist CGS 19755 (cis-4-phosphonomethyl-2-piperidinecarboxylic acid) has been prepared by applying Minisci reaction conditions [formamide, hydrogen peroxide, iron(II) sulfate] to ethyl isonicotinate, reduction of the ester with sodium borohydride, alcoholysis of the 2-carboxamide, formation of 4-(diethylphosphonomethyl)-2-pyridinecarboxylate, hydrogenation of the pyridine nucleus, and acid hydrolysis. The overall, unoptimized yield was around 11%. The procedure employs cheap starting materials, is practical and avoids the use of toxic and hazardous cyanotrimethylsilane which is used in the published procedure.</p>","PeriodicalId":76966,"journal":{"name":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","volume":"49 3","pages":"230-2"},"PeriodicalIF":0.0000,"publicationDate":"1995-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"6","resultStr":"{\"title\":\"An alternative synthesis of the NMDA antagonist CGS 19755 via free radical carbamoylation of ethyl isonicotinate.\",\"authors\":\"I Martin, J Anvelt, L Vares, I Kühn, A Claesson\",\"doi\":\"10.3891/acta.chem.scand.49-0230\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>The NMDA antagonist CGS 19755 (cis-4-phosphonomethyl-2-piperidinecarboxylic acid) has been prepared by applying Minisci reaction conditions [formamide, hydrogen peroxide, iron(II) sulfate] to ethyl isonicotinate, reduction of the ester with sodium borohydride, alcoholysis of the 2-carboxamide, formation of 4-(diethylphosphonomethyl)-2-pyridinecarboxylate, hydrogenation of the pyridine nucleus, and acid hydrolysis. The overall, unoptimized yield was around 11%. The procedure employs cheap starting materials, is practical and avoids the use of toxic and hazardous cyanotrimethylsilane which is used in the published procedure.</p>\",\"PeriodicalId\":76966,\"journal\":{\"name\":\"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)\",\"volume\":\"49 3\",\"pages\":\"230-2\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"1995-03-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"6\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.3891/acta.chem.scand.49-0230\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.3891/acta.chem.scand.49-0230","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
An alternative synthesis of the NMDA antagonist CGS 19755 via free radical carbamoylation of ethyl isonicotinate.
The NMDA antagonist CGS 19755 (cis-4-phosphonomethyl-2-piperidinecarboxylic acid) has been prepared by applying Minisci reaction conditions [formamide, hydrogen peroxide, iron(II) sulfate] to ethyl isonicotinate, reduction of the ester with sodium borohydride, alcoholysis of the 2-carboxamide, formation of 4-(diethylphosphonomethyl)-2-pyridinecarboxylate, hydrogenation of the pyridine nucleus, and acid hydrolysis. The overall, unoptimized yield was around 11%. The procedure employs cheap starting materials, is practical and avoids the use of toxic and hazardous cyanotrimethylsilane which is used in the published procedure.
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