A Convenient Synthesis of (−)-Paroxetine
A convenient synthesis of the antidepressant paroxetine starting from 1‐benzyl‐4‐piperidone (2) is reported. A stereoselective reduction resulted in cis‐piperidine‐3‐methanol [(+)‐6]. The reaction between cis‐piperidine‐3‐methanol mesylate (7) and sesamol led to benzyl‐protected trans‐paroxetine (9)...
Gespeichert in:
| Veröffentlicht in: | European journal of organic chemistry 2004-08, Vol.2004 (15), p.3336-3339 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 3339 |
|---|---|
| container_issue | 15 |
| container_start_page | 3336 |
| container_title | European journal of organic chemistry |
| container_volume | 2004 |
| creator | Czibula, László Nemes, András Sebök, Ferenc Szántay Jr, Csaba Mák, Marianna |
| description | A convenient synthesis of the antidepressant paroxetine starting from 1‐benzyl‐4‐piperidone (2) is reported. A stereoselective reduction resulted in cis‐piperidine‐3‐methanol [(+)‐6]. The reaction between cis‐piperidine‐3‐methanol mesylate (7) and sesamol led to benzyl‐protected trans‐paroxetine (9) through an inversion reaction of the stereogenic center at position 3. The latter compound was deprotected by hydrogenolysis. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004) |
| doi_str_mv | 10.1002/ejoc.200400067 |
| format | Article |
| fullrecord | <record><control><sourceid>wiley_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1002_ejoc_200400067</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>EJOC200400067</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3257-73e3fcbab29931d23a2c8a4104ff981f090071b5771aa4cb7bdb90eabe23bb9f3</originalsourceid><addsrcrecordid>eNqFj81Kw0AUhQdRsFa3rrNUYeKdmSTTWZbQH2uxgkrFzTCT3sHUmkgmaPsGrn1En8SUSHHn6h645zvwEXLKIGQA_BKXZRZygAgAErlHOgyUopAo2G9yJCLKlHg8JEfeL5uKShLWIRf9IC2LdyxyLOrgblPUz-hzH5QuOPv-_Dqnt6Yq11jnBR6TA2dWHk9-b5c8DAf36ZhOZ6OrtD-lmeCxpFKgcJk1lisl2IILw7OeiRhEzqkec6AAJLOxlMyYKLPSLqwCNBa5sFY50SVhu5tVpfcVOv1W5a-m2mgGemuqt6Z6Z9oAqgU-8hVu_mnrwWSW_mVpy-a-xvWONdWLbr4y1vObkY6f5mO4nnA9FT-0HWbr</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>A Convenient Synthesis of (−)-Paroxetine</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Czibula, László ; Nemes, András ; Sebök, Ferenc ; Szántay Jr, Csaba ; Mák, Marianna</creator><creatorcontrib>Czibula, László ; Nemes, András ; Sebök, Ferenc ; Szántay Jr, Csaba ; Mák, Marianna</creatorcontrib><description>A convenient synthesis of the antidepressant paroxetine starting from 1‐benzyl‐4‐piperidone (2) is reported. A stereoselective reduction resulted in cis‐piperidine‐3‐methanol [(+)‐6]. The reaction between cis‐piperidine‐3‐methanol mesylate (7) and sesamol led to benzyl‐protected trans‐paroxetine (9) through an inversion reaction of the stereogenic center at position 3. The latter compound was deprotected by hydrogenolysis. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.200400067</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Antidepressants ; Azabicycloheptane intermediates ; Hydrogenation ; Neighboring-group effects</subject><ispartof>European journal of organic chemistry, 2004-08, Vol.2004 (15), p.3336-3339</ispartof><rights>Copyright © 2004 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3257-73e3fcbab29931d23a2c8a4104ff981f090071b5771aa4cb7bdb90eabe23bb9f3</citedby><cites>FETCH-LOGICAL-c3257-73e3fcbab29931d23a2c8a4104ff981f090071b5771aa4cb7bdb90eabe23bb9f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.200400067$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1412,27905,27906,45556</link.rule.ids></links><search><creatorcontrib>Czibula, László</creatorcontrib><creatorcontrib>Nemes, András</creatorcontrib><creatorcontrib>Sebök, Ferenc</creatorcontrib><creatorcontrib>Szántay Jr, Csaba</creatorcontrib><creatorcontrib>Mák, Marianna</creatorcontrib><title>A Convenient Synthesis of (−)-Paroxetine</title><title>European journal of organic chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>A convenient synthesis of the antidepressant paroxetine starting from 1‐benzyl‐4‐piperidone (2) is reported. A stereoselective reduction resulted in cis‐piperidine‐3‐methanol [(+)‐6]. The reaction between cis‐piperidine‐3‐methanol mesylate (7) and sesamol led to benzyl‐protected trans‐paroxetine (9) through an inversion reaction of the stereogenic center at position 3. The latter compound was deprotected by hydrogenolysis. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)</description><subject>Antidepressants</subject><subject>Azabicycloheptane intermediates</subject><subject>Hydrogenation</subject><subject>Neighboring-group effects</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNqFj81Kw0AUhQdRsFa3rrNUYeKdmSTTWZbQH2uxgkrFzTCT3sHUmkgmaPsGrn1En8SUSHHn6h645zvwEXLKIGQA_BKXZRZygAgAErlHOgyUopAo2G9yJCLKlHg8JEfeL5uKShLWIRf9IC2LdyxyLOrgblPUz-hzH5QuOPv-_Dqnt6Yq11jnBR6TA2dWHk9-b5c8DAf36ZhOZ6OrtD-lmeCxpFKgcJk1lisl2IILw7OeiRhEzqkec6AAJLOxlMyYKLPSLqwCNBa5sFY50SVhu5tVpfcVOv1W5a-m2mgGemuqt6Z6Z9oAqgU-8hVu_mnrwWSW_mVpy-a-xvWONdWLbr4y1vObkY6f5mO4nnA9FT-0HWbr</recordid><startdate>200408</startdate><enddate>200408</enddate><creator>Czibula, László</creator><creator>Nemes, András</creator><creator>Sebök, Ferenc</creator><creator>Szántay Jr, Csaba</creator><creator>Mák, Marianna</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200408</creationdate><title>A Convenient Synthesis of (−)-Paroxetine</title><author>Czibula, László ; Nemes, András ; Sebök, Ferenc ; Szántay Jr, Csaba ; Mák, Marianna</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3257-73e3fcbab29931d23a2c8a4104ff981f090071b5771aa4cb7bdb90eabe23bb9f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Antidepressants</topic><topic>Azabicycloheptane intermediates</topic><topic>Hydrogenation</topic><topic>Neighboring-group effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Czibula, László</creatorcontrib><creatorcontrib>Nemes, András</creatorcontrib><creatorcontrib>Sebök, Ferenc</creatorcontrib><creatorcontrib>Szántay Jr, Csaba</creatorcontrib><creatorcontrib>Mák, Marianna</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Czibula, László</au><au>Nemes, András</au><au>Sebök, Ferenc</au><au>Szántay Jr, Csaba</au><au>Mák, Marianna</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Convenient Synthesis of (−)-Paroxetine</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2004-08</date><risdate>2004</risdate><volume>2004</volume><issue>15</issue><spage>3336</spage><epage>3339</epage><pages>3336-3339</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>A convenient synthesis of the antidepressant paroxetine starting from 1‐benzyl‐4‐piperidone (2) is reported. A stereoselective reduction resulted in cis‐piperidine‐3‐methanol [(+)‐6]. The reaction between cis‐piperidine‐3‐methanol mesylate (7) and sesamol led to benzyl‐protected trans‐paroxetine (9) through an inversion reaction of the stereogenic center at position 3. The latter compound was deprotected by hydrogenolysis. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.200400067</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1434-193X |
| ispartof | European journal of organic chemistry, 2004-08, Vol.2004 (15), p.3336-3339 |
| issn | 1434-193X 1099-0690 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_ejoc_200400067 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Antidepressants Azabicycloheptane intermediates Hydrogenation Neighboring-group effects |
| title | A Convenient Synthesis of (−)-Paroxetine |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-19T05%3A13%3A08IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-wiley_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=A%20Convenient%20Synthesis%20of%20(%E2%88%92)-Paroxetine&rft.jtitle=European%20journal%20of%20organic%20chemistry&rft.au=Czibula,%20L%C3%A1szl%C3%B3&rft.date=2004-08&rft.volume=2004&rft.issue=15&rft.spage=3336&rft.epage=3339&rft.pages=3336-3339&rft.issn=1434-193X&rft.eissn=1099-0690&rft_id=info:doi/10.1002/ejoc.200400067&rft_dat=%3Cwiley_cross%3EEJOC200400067%3C/wiley_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true |