Enantioselective phase-transfer catalyzed alkylation of 1-methyl-7-methoxy-2-tetralone: an effective route to dezocine
In order to prepare asymmetrically (R)-(+)-1-(5-bromopentyl)-1-methyl-7-methoxy-2-tetralone (3a), a key intermediate of dezocine, 17 cinchona alkaloid-derived catalysts were prepared and screened for the enantioselective alkylation of 1-methyl-7-methoxy-2-tetralone with 1,5-dibromopentane, and the b...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2018-06-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.14.119 |
| _version_ | 1818619872508116992 |
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| author | Ruipeng Li Zhenren Liu Liang Chen Jing Pan Weicheng Zhou |
| author_facet | Ruipeng Li Zhenren Liu Liang Chen Jing Pan Weicheng Zhou |
| author_sort | Ruipeng Li |
| collection | DOAJ |
| description | In order to prepare asymmetrically (R)-(+)-1-(5-bromopentyl)-1-methyl-7-methoxy-2-tetralone (3a), a key intermediate of dezocine, 17 cinchona alkaloid-derived catalysts were prepared and screened for the enantioselective alkylation of 1-methyl-7-methoxy-2-tetralone with 1,5-dibromopentane, and the best catalyst (C7) was identified. In addition, optimizations of the alkylation were carried out so that the process became practical and effective. |
| first_indexed | 2024-12-16T17:44:23Z |
| format | Article |
| id | doaj.art-9e0677d30eaa4a63916efd5729d95631 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-16T17:44:23Z |
| publishDate | 2018-06-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-9e0677d30eaa4a63916efd5729d956312022-12-21T22:22:31ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972018-06-011411421142710.3762/bjoc.14.1191860-5397-14-119Enantioselective phase-transfer catalyzed alkylation of 1-methyl-7-methoxy-2-tetralone: an effective route to dezocineRuipeng Li0Zhenren Liu1Liang Chen2Jing Pan3Weicheng Zhou4State Key Lab of New Drug & Pharmaceutical Process, Shanghai Key Lab of Anti-Infectives, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, No. 285, Gebaini Rd., Shanghai 201203, P. R. of ChinaState Key Lab of New Drug & Pharmaceutical Process, Shanghai Key Lab of Anti-Infectives, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, No. 285, Gebaini Rd., Shanghai 201203, P. R. of ChinaState Key Lab of New Drug & Pharmaceutical Process, Shanghai Key Lab of Anti-Infectives, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, No. 285, Gebaini Rd., Shanghai 201203, P. R. of ChinaState Key Lab of New Drug & Pharmaceutical Process, Shanghai Key Lab of Anti-Infectives, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, No. 285, Gebaini Rd., Shanghai 201203, P. R. of ChinaState Key Lab of New Drug & Pharmaceutical Process, Shanghai Key Lab of Anti-Infectives, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, No. 285, Gebaini Rd., Shanghai 201203, P. R. of ChinaIn order to prepare asymmetrically (R)-(+)-1-(5-bromopentyl)-1-methyl-7-methoxy-2-tetralone (3a), a key intermediate of dezocine, 17 cinchona alkaloid-derived catalysts were prepared and screened for the enantioselective alkylation of 1-methyl-7-methoxy-2-tetralone with 1,5-dibromopentane, and the best catalyst (C7) was identified. In addition, optimizations of the alkylation were carried out so that the process became practical and effective.https://doi.org/10.3762/bjoc.14.119alkylationasymmetric catalysiscinchonidinedezocine |
| spellingShingle | Ruipeng Li Zhenren Liu Liang Chen Jing Pan Weicheng Zhou Enantioselective phase-transfer catalyzed alkylation of 1-methyl-7-methoxy-2-tetralone: an effective route to dezocine Beilstein Journal of Organic Chemistry alkylation asymmetric catalysis cinchonidine dezocine |
| title | Enantioselective phase-transfer catalyzed alkylation of 1-methyl-7-methoxy-2-tetralone: an effective route to dezocine |
| title_full | Enantioselective phase-transfer catalyzed alkylation of 1-methyl-7-methoxy-2-tetralone: an effective route to dezocine |
| title_fullStr | Enantioselective phase-transfer catalyzed alkylation of 1-methyl-7-methoxy-2-tetralone: an effective route to dezocine |
| title_full_unstemmed | Enantioselective phase-transfer catalyzed alkylation of 1-methyl-7-methoxy-2-tetralone: an effective route to dezocine |
| title_short | Enantioselective phase-transfer catalyzed alkylation of 1-methyl-7-methoxy-2-tetralone: an effective route to dezocine |
| title_sort | enantioselective phase transfer catalyzed alkylation of 1 methyl 7 methoxy 2 tetralone an effective route to dezocine |
| topic | alkylation asymmetric catalysis cinchonidine dezocine |
| url | https://doi.org/10.3762/bjoc.14.119 |
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