Concise, efficient and highly selective asymmetric synthesis of (+)-(3S,4R)-cisapride
A concise asymmetric synthesis of the gastroprokinetic agent (+)-(3S,4R)-cisapride {(+)-(3S,4R)-N(1)-[3′-(4″-fluorophenoxy) propyl]-3-methoxy-4-(2″′-methoxy-4″′-amino- 5″′-chlorobenzamido)piperidine} from commercially available starting materials has been developed. The key step of this synthesis em...
| Κύριοι συγγραφείς: | , , , , |
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| Μορφή: | Journal article |
| Γλώσσα: | English |
| Έκδοση: |
2011
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| _version_ | 1826264774698074112 |
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| author | Davies, S Huckvale, R Lorkin, T Roberts, P Thomson, J |
| author_facet | Davies, S Huckvale, R Lorkin, T Roberts, P Thomson, J |
| author_sort | Davies, S |
| collection | OXFORD |
| description | A concise asymmetric synthesis of the gastroprokinetic agent (+)-(3S,4R)-cisapride {(+)-(3S,4R)-N(1)-[3′-(4″-fluorophenoxy) propyl]-3-methoxy-4-(2″′-methoxy-4″′-amino- 5″′-chlorobenzamido)piperidine} from commercially available starting materials has been developed. The key step of this synthesis employs the diastereoselective conjugate addition of lithium (R)-N-benzyl-N-(α- methylbenzyl)amide to tert-butyl 5-[N-3′-(4″-fluorophenoxy)propyl-N- allylamino]pent-2-enoate and in situ enolate oxidation with (-)- camphorsulfonyloxaziridine to set the (3S,4R)-configuration found within the piperidine ring of the product. This synthesis proceeds in 9 steps from commercially available 1-(4′-fluorophenoxy)-3-bromopropane with an overall yield of 19%. © 2011 Elsevier Ltd. All rights reserved. |
| first_indexed | 2024-03-06T20:13:15Z |
| format | Journal article |
| id | oxford-uuid:2b4c1459-b58a-4dbd-bcb9-83a6dc80d31c |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T20:13:15Z |
| publishDate | 2011 |
| record_format | dspace |
| spelling | oxford-uuid:2b4c1459-b58a-4dbd-bcb9-83a6dc80d31c2022-03-26T12:30:04ZConcise, efficient and highly selective asymmetric synthesis of (+)-(3S,4R)-cisaprideJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:2b4c1459-b58a-4dbd-bcb9-83a6dc80d31cEnglishSymplectic Elements at Oxford2011Davies, SHuckvale, RLorkin, TRoberts, PThomson, JA concise asymmetric synthesis of the gastroprokinetic agent (+)-(3S,4R)-cisapride {(+)-(3S,4R)-N(1)-[3′-(4″-fluorophenoxy) propyl]-3-methoxy-4-(2″′-methoxy-4″′-amino- 5″′-chlorobenzamido)piperidine} from commercially available starting materials has been developed. The key step of this synthesis employs the diastereoselective conjugate addition of lithium (R)-N-benzyl-N-(α- methylbenzyl)amide to tert-butyl 5-[N-3′-(4″-fluorophenoxy)propyl-N- allylamino]pent-2-enoate and in situ enolate oxidation with (-)- camphorsulfonyloxaziridine to set the (3S,4R)-configuration found within the piperidine ring of the product. This synthesis proceeds in 9 steps from commercially available 1-(4′-fluorophenoxy)-3-bromopropane with an overall yield of 19%. © 2011 Elsevier Ltd. All rights reserved. |
| spellingShingle | Davies, S Huckvale, R Lorkin, T Roberts, P Thomson, J Concise, efficient and highly selective asymmetric synthesis of (+)-(3S,4R)-cisapride |
| title | Concise, efficient and highly selective asymmetric synthesis of (+)-(3S,4R)-cisapride |
| title_full | Concise, efficient and highly selective asymmetric synthesis of (+)-(3S,4R)-cisapride |
| title_fullStr | Concise, efficient and highly selective asymmetric synthesis of (+)-(3S,4R)-cisapride |
| title_full_unstemmed | Concise, efficient and highly selective asymmetric synthesis of (+)-(3S,4R)-cisapride |
| title_short | Concise, efficient and highly selective asymmetric synthesis of (+)-(3S,4R)-cisapride |
| title_sort | concise efficient and highly selective asymmetric synthesis of 3s 4r cisapride |
| work_keys_str_mv | AT daviess conciseefficientandhighlyselectiveasymmetricsynthesisof3s4rcisapride AT huckvaler conciseefficientandhighlyselectiveasymmetricsynthesisof3s4rcisapride AT lorkint conciseefficientandhighlyselectiveasymmetricsynthesisof3s4rcisapride AT robertsp conciseefficientandhighlyselectiveasymmetricsynthesisof3s4rcisapride AT thomsonj conciseefficientandhighlyselectiveasymmetricsynthesisof3s4rcisapride |