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Synthesis of (−)- and (+)-2-hydroxy-6-keto-N-methylmorphinans, their O-methyl ethers, and 2-deoxy congeners
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| Zeitschriftentitel: | Canadian Journal of Chemistry |
|---|---|
| Personen und Körperschaften: | , |
| In: | Canadian Journal of Chemistry, 60, 1982, 24, S. 3055-3060 |
| Format: | E-Article |
| Sprache: | Französisch |
| veröffentlicht: |
Canadian Science Publishing
|
| Schlagwörter: |
| author_facet |
Schmidhammer, Helmut Brossi, Arnold Schmidhammer, Helmut Brossi, Arnold |
|---|---|
| author |
Schmidhammer, Helmut Brossi, Arnold |
| spellingShingle |
Schmidhammer, Helmut Brossi, Arnold Canadian Journal of Chemistry Synthesis of (−)- and (+)-2-hydroxy-6-keto-N-methylmorphinans, their O-methyl ethers, and 2-deoxy congeners Organic Chemistry General Chemistry Catalysis |
| author_sort |
schmidhammer, helmut |
| spelling |
Schmidhammer, Helmut Brossi, Arnold 0008-4042 1480-3291 Canadian Science Publishing Organic Chemistry General Chemistry Catalysis http://dx.doi.org/10.1139/v82-437 <jats:p> Bischler–Napieralski cyclization of the known phenylacetamide 1, followed by selective ether cleavage of the 3,4-dihydroisoquinoline 2 and sodium borohydride reduction, afforded the tetrahydroisoquinoline 4. Optical resolution of 4 with tartaric acid gave the optical isomers 4a,b, which were converted into the 6-ketomorphinans 9a,b and their O-methyl ethers 10a,b by the following reaction sequence: Birch reduction, N-formylation of the dihydro bases, Grewe cyclization, removal of the N-formyl protecting groups, reductive N-methylation, and O-methylation. The 2-deoxy congeners 12a,b were obtained from 9a,b by phenyltetrazolylation, and catalytic removal of the heterocyclic etherfunction. The (−)-enantiomer 12a obtained by this synthesis was identical with material prepared from natural morphine, and exhibited the high antinociceptive potency already reported. </jats:p> Synthesis of (−)- and (+)-2-hydroxy-6-keto-<i>N</i>-methylmorphinans, their <i>O</i>-methyl ethers, and 2-deoxy congeners Canadian Journal of Chemistry |
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Canadian Science Publishing, 1982 |
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Canadian Science Publishing, 1982 |
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1480-3291 0008-4042 |
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1982 |
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Canadian Science Publishing |
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Canadian Journal of Chemistry |
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| title |
Synthesis of (−)- and (+)-2-hydroxy-6-keto-N-methylmorphinans, their O-methyl ethers, and 2-deoxy congeners |
| title_unstemmed |
Synthesis of (−)- and (+)-2-hydroxy-6-keto-N-methylmorphinans, their O-methyl ethers, and 2-deoxy congeners |
| title_full |
Synthesis of (−)- and (+)-2-hydroxy-6-keto-N-methylmorphinans, their O-methyl ethers, and 2-deoxy congeners |
| title_fullStr |
Synthesis of (−)- and (+)-2-hydroxy-6-keto-N-methylmorphinans, their O-methyl ethers, and 2-deoxy congeners |
| title_full_unstemmed |
Synthesis of (−)- and (+)-2-hydroxy-6-keto-N-methylmorphinans, their O-methyl ethers, and 2-deoxy congeners |
| title_short |
Synthesis of (−)- and (+)-2-hydroxy-6-keto-N-methylmorphinans, their O-methyl ethers, and 2-deoxy congeners |
| title_sort |
synthesis of (−)- and (+)-2-hydroxy-6-keto-<i>n</i>-methylmorphinans, their <i>o</i>-methyl ethers, and 2-deoxy congeners |
| topic |
Organic Chemistry General Chemistry Catalysis |
| url |
http://dx.doi.org/10.1139/v82-437 |
| publishDate |
1982 |
| physical |
3055-3060 |
| description |
<jats:p> Bischler–Napieralski cyclization of the known phenylacetamide 1, followed by selective ether cleavage of the 3,4-dihydroisoquinoline 2 and sodium borohydride reduction, afforded the tetrahydroisoquinoline 4. Optical resolution of 4 with tartaric acid gave the optical isomers 4a,b, which were converted into the 6-ketomorphinans 9a,b and their O-methyl ethers 10a,b by the following reaction sequence: Birch reduction, N-formylation of the dihydro bases, Grewe cyclization, removal of the N-formyl protecting groups, reductive N-methylation, and O-methylation. The 2-deoxy congeners 12a,b were obtained from 9a,b by phenyltetrazolylation, and catalytic removal of the heterocyclic etherfunction. The (−)-enantiomer 12a obtained by this synthesis was identical with material prepared from natural morphine, and exhibited the high antinociceptive potency already reported. </jats:p> |
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| author | Schmidhammer, Helmut, Brossi, Arnold |
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| author_sort | schmidhammer, helmut |
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| container_start_page | 3055 |
| container_title | Canadian Journal of Chemistry |
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| description | <jats:p> Bischler–Napieralski cyclization of the known phenylacetamide 1, followed by selective ether cleavage of the 3,4-dihydroisoquinoline 2 and sodium borohydride reduction, afforded the tetrahydroisoquinoline 4. Optical resolution of 4 with tartaric acid gave the optical isomers 4a,b, which were converted into the 6-ketomorphinans 9a,b and their O-methyl ethers 10a,b by the following reaction sequence: Birch reduction, N-formylation of the dihydro bases, Grewe cyclization, removal of the N-formyl protecting groups, reductive N-methylation, and O-methylation. The 2-deoxy congeners 12a,b were obtained from 9a,b by phenyltetrazolylation, and catalytic removal of the heterocyclic etherfunction. The (−)-enantiomer 12a obtained by this synthesis was identical with material prepared from natural morphine, and exhibited the high antinociceptive potency already reported. </jats:p> |
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| imprint | Canadian Science Publishing, 1982 |
| imprint_str_mv | Canadian Science Publishing, 1982 |
| institution | DE-Bn3, DE-Brt1, DE-Zwi2, DE-D161, DE-Gla1, DE-Zi4, DE-15, DE-Pl11, DE-Rs1, DE-105, DE-14, DE-Ch1, DE-L229, DE-D275 |
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| series | Canadian Journal of Chemistry |
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| spelling | Schmidhammer, Helmut Brossi, Arnold 0008-4042 1480-3291 Canadian Science Publishing Organic Chemistry General Chemistry Catalysis http://dx.doi.org/10.1139/v82-437 <jats:p> Bischler–Napieralski cyclization of the known phenylacetamide 1, followed by selective ether cleavage of the 3,4-dihydroisoquinoline 2 and sodium borohydride reduction, afforded the tetrahydroisoquinoline 4. Optical resolution of 4 with tartaric acid gave the optical isomers 4a,b, which were converted into the 6-ketomorphinans 9a,b and their O-methyl ethers 10a,b by the following reaction sequence: Birch reduction, N-formylation of the dihydro bases, Grewe cyclization, removal of the N-formyl protecting groups, reductive N-methylation, and O-methylation. The 2-deoxy congeners 12a,b were obtained from 9a,b by phenyltetrazolylation, and catalytic removal of the heterocyclic etherfunction. The (−)-enantiomer 12a obtained by this synthesis was identical with material prepared from natural morphine, and exhibited the high antinociceptive potency already reported. </jats:p> Synthesis of (−)- and (+)-2-hydroxy-6-keto-<i>N</i>-methylmorphinans, their <i>O</i>-methyl ethers, and 2-deoxy congeners Canadian Journal of Chemistry |
| spellingShingle | Schmidhammer, Helmut, Brossi, Arnold, Canadian Journal of Chemistry, Synthesis of (−)- and (+)-2-hydroxy-6-keto-N-methylmorphinans, their O-methyl ethers, and 2-deoxy congeners, Organic Chemistry, General Chemistry, Catalysis |
| title | Synthesis of (−)- and (+)-2-hydroxy-6-keto-N-methylmorphinans, their O-methyl ethers, and 2-deoxy congeners |
| title_full | Synthesis of (−)- and (+)-2-hydroxy-6-keto-N-methylmorphinans, their O-methyl ethers, and 2-deoxy congeners |
| title_fullStr | Synthesis of (−)- and (+)-2-hydroxy-6-keto-N-methylmorphinans, their O-methyl ethers, and 2-deoxy congeners |
| title_full_unstemmed | Synthesis of (−)- and (+)-2-hydroxy-6-keto-N-methylmorphinans, their O-methyl ethers, and 2-deoxy congeners |
| title_short | Synthesis of (−)- and (+)-2-hydroxy-6-keto-N-methylmorphinans, their O-methyl ethers, and 2-deoxy congeners |
| title_sort | synthesis of (−)- and (+)-2-hydroxy-6-keto-<i>n</i>-methylmorphinans, their <i>o</i>-methyl ethers, and 2-deoxy congeners |
| title_unstemmed | Synthesis of (−)- and (+)-2-hydroxy-6-keto-N-methylmorphinans, their O-methyl ethers, and 2-deoxy congeners |
| topic | Organic Chemistry, General Chemistry, Catalysis |
| url | http://dx.doi.org/10.1139/v82-437 |