Yufei Li, Lan Jiang, Li Zhang, Jingyu Wang, Peng Xiang, J. Pan, Xiangnan Hu
{"title":"维格列汀中间体的高效合成","authors":"Yufei Li, Lan Jiang, Li Zhang, Jingyu Wang, Peng Xiang, J. Pan, Xiangnan Hu","doi":"10.56042/ijcb.v60i8.30478","DOIUrl":null,"url":null,"abstract":"Efficient and high yielding methods for the preparation of vildagliptin 1 intermediate of (S)-1-(2-chloroacetyl) pyrrolidine-2-carbonitrile 2 and 3-amino-1-adamantane alcohol 3 respectively have been described. (S)-1-(2-Chloroacetyl) pyrrolidine-2-carbonitrile 2 has been synthesized from L-proline 2a via chloroacetyl chloride, performed with acetonitrile in the presence of sulfuric acid via one-pot reactions. 3-Amino-1-adamantane alcohol 3 has been prepared from amantadine hydrochloride via oxidation by sulfuric acid/nitric acid and boric acid as catalyst, and has been subjected to ethanol extraction. The overall yield is about 95%.","PeriodicalId":13458,"journal":{"name":"Indian Journal of Chemistry Section B-organic Chemistry Including Medicinal Chemistry","volume":"8 1","pages":""},"PeriodicalIF":0.5000,"publicationDate":"2021-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"An efficient synthesis of Vildagliptin intermediates\",\"authors\":\"Yufei Li, Lan Jiang, Li Zhang, Jingyu Wang, Peng Xiang, J. Pan, Xiangnan Hu\",\"doi\":\"10.56042/ijcb.v60i8.30478\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Efficient and high yielding methods for the preparation of vildagliptin 1 intermediate of (S)-1-(2-chloroacetyl) pyrrolidine-2-carbonitrile 2 and 3-amino-1-adamantane alcohol 3 respectively have been described. (S)-1-(2-Chloroacetyl) pyrrolidine-2-carbonitrile 2 has been synthesized from L-proline 2a via chloroacetyl chloride, performed with acetonitrile in the presence of sulfuric acid via one-pot reactions. 3-Amino-1-adamantane alcohol 3 has been prepared from amantadine hydrochloride via oxidation by sulfuric acid/nitric acid and boric acid as catalyst, and has been subjected to ethanol extraction. The overall yield is about 95%.\",\"PeriodicalId\":13458,\"journal\":{\"name\":\"Indian Journal of Chemistry Section B-organic Chemistry Including Medicinal Chemistry\",\"volume\":\"8 1\",\"pages\":\"\"},\"PeriodicalIF\":0.5000,\"publicationDate\":\"2021-10-07\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Indian Journal of Chemistry Section B-organic Chemistry Including Medicinal Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.56042/ijcb.v60i8.30478\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"Pharmacology, Toxicology and Pharmaceutics\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Indian Journal of Chemistry Section B-organic Chemistry Including Medicinal Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.56042/ijcb.v60i8.30478","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"Pharmacology, Toxicology and Pharmaceutics","Score":null,"Total":0}
An efficient synthesis of Vildagliptin intermediates
Efficient and high yielding methods for the preparation of vildagliptin 1 intermediate of (S)-1-(2-chloroacetyl) pyrrolidine-2-carbonitrile 2 and 3-amino-1-adamantane alcohol 3 respectively have been described. (S)-1-(2-Chloroacetyl) pyrrolidine-2-carbonitrile 2 has been synthesized from L-proline 2a via chloroacetyl chloride, performed with acetonitrile in the presence of sulfuric acid via one-pot reactions. 3-Amino-1-adamantane alcohol 3 has been prepared from amantadine hydrochloride via oxidation by sulfuric acid/nitric acid and boric acid as catalyst, and has been subjected to ethanol extraction. The overall yield is about 95%.
期刊介绍:
Indian Journal of Chemistry (Section B) is a leading monthly journal in Organic and Medicinal Chemistry started publishing from 1976. It publishes papers on organic reaction mechanism, theoretical organic chemistry, structure-activity relationships, medicinal chemistry, synthesis of chiral compounds, bio-organic chemistry, enzymes in organic synthesis, reagents in organic synthesis, heterocyclic compounds, phytochemistry (natural products), amino acids, peptides and proteins, spectroscopy in characterization of organic compounds, chemoenzymatic and enantioselective synthesis of organic compounds, synthesis of fullerenes, metal-catalyzed asymmetric reactions, bioactive plant products and combinatorial chemistry. Apart from full length papers, notes and communications, the journal publishes short reviews on frontline areas under the column " advances in Contemporary Research".