- 9-Oxobenzomorphan process and intermediates
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Improved processes for preparing 2'-alkoxy-2,5-di-substituted-9-oxo-6,7-benzomorphans from benz[e]indolines and synthesis of the benz[e]indoline intermediates are described. A representative example involves synthesis of 9b-allyl-8-methoxy-3-methyl-5,9b-dihydrobenz[e]indoline and bromination thereof to 9b-allyl-4-bromo-8-methoxy-2,4,5,9b-tetrahydro-1H-benz[e]indole methylbromide which is then hydrolyzed with a weak base such as ammonium bicarbonate to provide 5-allyl-2'-methoxy-2-methyl-9-oxo-6,7-benzomorphan.
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- 9-Alkoxy-5-methyl-6,7-benzomorphans
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N-Substituted-9-alkoxy-5-methyl-6,7-benzomorphans have been found to possess potent narcotic agonist and/or antagonist activity. In particular, the compound 2-cyclopropylmethyl-2'-hydroxy-9α-methoxy-5-methyl-6,7-benzomorphan has been found to possess potent narcotic agonist and antagonist activity. These compounds are prepared by total synthesis and are not derived from opium alkaloids.
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- 3,14-Substituted-8-oxamorphinans
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N-Substituted-3-hydroxy-8-oxamorphinans have been found to possess potent narcotic agonist and/or antagonist activity. In particular, the compound l-N-cyclopropylmethyl-3-hydroxy-14β-methyl-8-oxamorphinan has been found to possess potent narcotic antagonist and agonist activity. These compounds are prepared by total synthesis and are not derived from opium alkaloids.
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