A facile method to synthesize vildagliptin
An efficient and high-yielding synthetic method for the preparation of vildagliptin via four steps is reported. The process starts from L-proline and involves a successful reaction with chloroacetyl chloride in tetrahydrofuran to afford (S)-1-(2-chloroacetyl)pyrrolidine-2-carboxylic acid, followed b...
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| Veröffentlicht in: | Journal of chemical research 2021-03, Vol.45 (3-4), p.305-309 |
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| container_end_page | 309 |
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| container_issue | 3-4 |
| container_start_page | 305 |
| container_title | Journal of chemical research |
| container_volume | 45 |
| creator | Zhang, Li Jiang, Lan Guan, Xiaoshu Cai, Linhong Wang, Jingyu Xiang, Peng Pan, Junyi Hu, Xiangnan |
| description | An efficient and high-yielding synthetic method for the preparation of vildagliptin via four steps is reported. The process starts from L-proline and involves a successful reaction with chloroacetyl chloride in tetrahydrofuran to afford (S)-1-(2-chloroacetyl)pyrrolidine-2-carboxylic acid, followed by a reaction with acetonitrile in the presence of sulfuric acid to give (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile. This is then reacted with 3-aminoadamantanol to give vildagliptin. 3-Aminoadamantanol is prepared from 1-aminoadamantane hydrochloride via oxidation with sulfuric acid/nitric acid and boric acid as the catalyst followed by ethanol extraction. The overall yield is 95%. |
| doi_str_mv | 10.1177/1747519820967123 |
| format | Article |
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The process starts from L-proline and involves a successful reaction with chloroacetyl chloride in tetrahydrofuran to afford (S)-1-(2-chloroacetyl)pyrrolidine-2-carboxylic acid, followed by a reaction with acetonitrile in the presence of sulfuric acid to give (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile. This is then reacted with 3-aminoadamantanol to give vildagliptin. 3-Aminoadamantanol is prepared from 1-aminoadamantane hydrochloride via oxidation with sulfuric acid/nitric acid and boric acid as the catalyst followed by ethanol extraction. 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The process starts from L-proline and involves a successful reaction with chloroacetyl chloride in tetrahydrofuran to afford (S)-1-(2-chloroacetyl)pyrrolidine-2-carboxylic acid, followed by a reaction with acetonitrile in the presence of sulfuric acid to give (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile. This is then reacted with 3-aminoadamantanol to give vildagliptin. 3-Aminoadamantanol is prepared from 1-aminoadamantane hydrochloride via oxidation with sulfuric acid/nitric acid and boric acid as the catalyst followed by ethanol extraction. The overall yield is 95%.</description><subject>Acetonitrile</subject><subject>Carboxylic acids</subject><subject>Ethanol</subject><subject>Nitric acid</subject><subject>Oxidation</subject><subject>Proline</subject><subject>Sulfuric acid</subject><subject>Tetrahydrofuran</subject><issn>1747-5198</issn><issn>2047-6507</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>AFRWT</sourceid><recordid>eNp1kM1Lw0AQxRdRMFbvHgPehOjsZDebHEvxCwpe9Bwm-9FuSZOYTYX615sQQRA8Dbz3e2_gMXbN4Y5zpe65EkryIkcoMsUxPWERglBJJkGdsmiyk8k_Zxch7ACEzAoesdtl7Ej72sZ7O2xbEw9tHI7NsLXBf9n409eGNrXvBt9csjNHdbBXP3fB3h8f3lbPyfr16WW1XCc6lXxIHAHmhqSyZHTFJeacnJCawKLRKiVl8kqLSTFU6Ioy45BI56gAKavSBbuZe7u-_TjYMJS79tA348sSJQoEkAWOFMyU7tsQeuvKrvd76o8lh3JapPy7yBhJ5kigjf0t_Zf_Bk6GYCU</recordid><startdate>202103</startdate><enddate>202103</enddate><creator>Zhang, Li</creator><creator>Jiang, Lan</creator><creator>Guan, Xiaoshu</creator><creator>Cai, Linhong</creator><creator>Wang, Jingyu</creator><creator>Xiang, Peng</creator><creator>Pan, Junyi</creator><creator>Hu, Xiangnan</creator><general>SAGE Publications</general><general>Sage Publications Ltd</general><scope>AFRWT</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>202103</creationdate><title>A facile method to synthesize vildagliptin</title><author>Zhang, Li ; Jiang, Lan ; Guan, Xiaoshu ; Cai, Linhong ; Wang, Jingyu ; Xiang, Peng ; Pan, Junyi ; Hu, Xiangnan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c351t-fa028da57eadcb15281af45ca0e2dc73a7d8bc445cada9cba6df2aac82702a6b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Acetonitrile</topic><topic>Carboxylic acids</topic><topic>Ethanol</topic><topic>Nitric acid</topic><topic>Oxidation</topic><topic>Proline</topic><topic>Sulfuric acid</topic><topic>Tetrahydrofuran</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Li</creatorcontrib><creatorcontrib>Jiang, Lan</creatorcontrib><creatorcontrib>Guan, Xiaoshu</creatorcontrib><creatorcontrib>Cai, Linhong</creatorcontrib><creatorcontrib>Wang, Jingyu</creatorcontrib><creatorcontrib>Xiang, Peng</creatorcontrib><creatorcontrib>Pan, Junyi</creatorcontrib><creatorcontrib>Hu, Xiangnan</creatorcontrib><collection>Sage Journals GOLD Open Access 2024</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Journal of chemical research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Li</au><au>Jiang, Lan</au><au>Guan, Xiaoshu</au><au>Cai, Linhong</au><au>Wang, Jingyu</au><au>Xiang, Peng</au><au>Pan, Junyi</au><au>Hu, Xiangnan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A facile method to synthesize vildagliptin</atitle><jtitle>Journal of chemical research</jtitle><date>2021-03</date><risdate>2021</risdate><volume>45</volume><issue>3-4</issue><spage>305</spage><epage>309</epage><pages>305-309</pages><issn>1747-5198</issn><eissn>2047-6507</eissn><abstract>An efficient and high-yielding synthetic method for the preparation of vildagliptin via four steps is reported. The process starts from L-proline and involves a successful reaction with chloroacetyl chloride in tetrahydrofuran to afford (S)-1-(2-chloroacetyl)pyrrolidine-2-carboxylic acid, followed by a reaction with acetonitrile in the presence of sulfuric acid to give (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile. This is then reacted with 3-aminoadamantanol to give vildagliptin. 3-Aminoadamantanol is prepared from 1-aminoadamantane hydrochloride via oxidation with sulfuric acid/nitric acid and boric acid as the catalyst followed by ethanol extraction. The overall yield is 95%.</abstract><cop>London, England</cop><pub>SAGE Publications</pub><doi>10.1177/1747519820967123</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Journal of chemical research, 2021-03, Vol.45 (3-4), p.305-309 |
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| language | eng |
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| source | DOAJ Directory of Open Access Journals; Sage Journals GOLD Open Access 2024; Alma/SFX Local Collection |
| subjects | Acetonitrile Carboxylic acids Ethanol Nitric acid Oxidation Proline Sulfuric acid Tetrahydrofuran |
| title | A facile method to synthesize vildagliptin |
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