Method for preparing silodosin chiral intermediate
The present invention provides a method for synthesizing a silodosin intermediate with a high enantiomeric purity. The method comprises the steps of using 1-[3-(benzyloxy)propyl]-5-bromoindoline as the raw material, performing a bromine lithium exchange reaction with an organolithium reagent to obta...
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| creator | YAN MING WU LIANGYU HUANG TONGKUN |
| description | The present invention provides a method for synthesizing a silodosin intermediate with a high enantiomeric purity. The method comprises the steps of using 1-[3-(benzyloxy)propyl]-5-bromoindoline as the raw material, performing a bromine lithium exchange reaction with an organolithium reagent to obtain 1-[3-(benzyloxy)propyl]-5-lithiumindoline, performing a Weinreb amidization reaction with (R)-N-(alkoxycarbonyl)alanine to obtain the silodosin intermediate with a good yield and enantioselectivity. The method has the advantages of simple operation, cheap and easily-available raw materials, highenantiomeric purity of the product and no resolution step, and has extremely high application value for industrial preparation of silodosin.
本发明提供种合成高对映纯度的西洛多辛中间体的方法。该方法以1-[3-(苄氧基)丙基]-5-溴-吲哚啉为原料，与有机锂试剂进行溴锂交换反应，得到1-[3-(苄氧基)丙基]-5-锂-吲哚啉，再与(R)-N-烷氧羰基-丙氨酸Weinreb酰胺反应，以良好的产率和对映选择性得到西洛多辛中间体。该方法操作简单，原料廉价易得，产物对映纯度高，无需拆分步骤，对于西洛多辛的工业制备具有很高的应用价值。 |
| format | Patent |
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本发明提供种合成高对映纯度的西洛多辛中间体的方法。该方法以1-[3-(苄氧基)丙基]-5-溴-吲哚啉为原料，与有机锂试剂进行溴锂交换反应，得到1-[3-(苄氧基)丙基]-5-锂-吲哚啉，再与(R)-N-烷氧羰基-丙氨酸Weinreb酰胺反应，以良好的产率和对映选择性得到西洛多辛中间体。该方法操作简单，原料廉价易得，产物对映纯度高，无需拆分步骤，对于西洛多辛的工业制备具有很高的应用价值。</description><language>chi ; eng</language><subject>CHEMISTRY ; HETEROCYCLIC COMPOUNDS ; METALLURGY ; ORGANIC CHEMISTRY</subject><creationdate>2018</creationdate><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=20180330&DB=EPODOC&CC=CN&NR=107857720A$$EHTML$$P50$$Gepo$$Hfree_for_read</linktohtml><link.rule.ids>230,308,780,885,25564,76547</link.rule.ids><linktorsrc>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=20180330&DB=EPODOC&CC=CN&NR=107857720A$$EView_record_in_European_Patent_Office$$FView_record_in_$$GEuropean_Patent_Office$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>YAN MING</creatorcontrib><creatorcontrib>WU LIANGYU</creatorcontrib><creatorcontrib>HUANG TONGKUN</creatorcontrib><title>Method for preparing silodosin chiral intermediate</title><description>The present invention provides a method for synthesizing a silodosin intermediate with a high enantiomeric purity. The method comprises the steps of using 1-[3-(benzyloxy)propyl]-5-bromoindoline as the raw material, performing a bromine lithium exchange reaction with an organolithium reagent to obtain 1-[3-(benzyloxy)propyl]-5-lithiumindoline, performing a Weinreb amidization reaction with (R)-N-(alkoxycarbonyl)alanine to obtain the silodosin intermediate with a good yield and enantioselectivity. The method has the advantages of simple operation, cheap and easily-available raw materials, highenantiomeric purity of the product and no resolution step, and has extremely high application value for industrial preparation of silodosin.
本发明提供种合成高对映纯度的西洛多辛中间体的方法。该方法以1-[3-(苄氧基)丙基]-5-溴-吲哚啉为原料，与有机锂试剂进行溴锂交换反应，得到1-[3-(苄氧基)丙基]-5-锂-吲哚啉，再与(R)-N-烷氧羰基-丙氨酸Weinreb酰胺反应，以良好的产率和对映选择性得到西洛多辛中间体。该方法操作简单，原料廉价易得，产物对映纯度高，无需拆分步骤，对于西洛多辛的工业制备具有很高的应用价值。</description><subject>CHEMISTRY</subject><subject>HETEROCYCLIC COMPOUNDS</subject><subject>METALLURGY</subject><subject>ORGANIC CHEMISTRY</subject><fulltext>true</fulltext><rsrctype>patent</rsrctype><creationdate>2018</creationdate><recordtype>patent</recordtype><sourceid>EVB</sourceid><recordid>eNrjZDDyTS3JyE9RSMsvUigoSi1ILMrMS1cozszJT8kvzsxTSM7ILErMUcjMK0ktyk1NyUwsSeVhYE1LzClO5YXS3AyKbq4hzh66qQX58anFBYnJqXmpJfHOfoYG5ham5uZGBo7GxKgBAO9uLHU</recordid><startdate>20180330</startdate><enddate>20180330</enddate><creator>YAN MING</creator><creator>WU LIANGYU</creator><creator>HUANG TONGKUN</creator><scope>EVB</scope></search><sort><creationdate>20180330</creationdate><title>Method for preparing silodosin chiral intermediate</title><author>YAN MING ; WU LIANGYU ; HUANG TONGKUN</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-epo_espacenet_CN107857720A3</frbrgroupid><rsrctype>patents</rsrctype><prefilter>patents</prefilter><language>chi ; eng</language><creationdate>2018</creationdate><topic>CHEMISTRY</topic><topic>HETEROCYCLIC COMPOUNDS</topic><topic>METALLURGY</topic><topic>ORGANIC CHEMISTRY</topic><toplevel>online_resources</toplevel><creatorcontrib>YAN MING</creatorcontrib><creatorcontrib>WU LIANGYU</creatorcontrib><creatorcontrib>HUANG TONGKUN</creatorcontrib><collection>esp@cenet</collection></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>YAN MING</au><au>WU LIANGYU</au><au>HUANG TONGKUN</au><format>patent</format><genre>patent</genre><ristype>GEN</ristype><title>Method for preparing silodosin chiral intermediate</title><date>2018-03-30</date><risdate>2018</risdate><abstract>The present invention provides a method for synthesizing a silodosin intermediate with a high enantiomeric purity. The method comprises the steps of using 1-[3-(benzyloxy)propyl]-5-bromoindoline as the raw material, performing a bromine lithium exchange reaction with an organolithium reagent to obtain 1-[3-(benzyloxy)propyl]-5-lithiumindoline, performing a Weinreb amidization reaction with (R)-N-(alkoxycarbonyl)alanine to obtain the silodosin intermediate with a good yield and enantioselectivity. The method has the advantages of simple operation, cheap and easily-available raw materials, highenantiomeric purity of the product and no resolution step, and has extremely high application value for industrial preparation of silodosin.
本发明提供种合成高对映纯度的西洛多辛中间体的方法。该方法以1-[3-(苄氧基)丙基]-5-溴-吲哚啉为原料，与有机锂试剂进行溴锂交换反应，得到1-[3-(苄氧基)丙基]-5-锂-吲哚啉，再与(R)-N-烷氧羰基-丙氨酸Weinreb酰胺反应，以良好的产率和对映选择性得到西洛多辛中间体。该方法操作简单，原料廉价易得，产物对映纯度高，无需拆分步骤，对于西洛多辛的工业制备具有很高的应用价值。</abstract><oa>free_for_read</oa></addata></record> |
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| title | Method for preparing silodosin chiral intermediate |
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