78815-69-7Relevant academic research and scientific papers
Bridged-ring Nitrogen Compounds. Part 8. The Chemistry of the 2,6-Methano-3-benzazonine Ring System.
McKnight, William E.,Proctor, George R.,Sneddon, Andrew H.,Scopes, David I. C.
, p. 642 - 679 (2007/10/02)
The previously described route to 1,2,3,4,5,6-hexahydro-3-methyl-2,6-methano-3-benzazonin-7-one (1a) has been fully investigated with particular reference to the Stevens rearrangement of N-benzyl-4-ethoxycarbonyl-1,2,3,6-tetrahydro-1-methylpyridinium bromide which leads to two basic products.The major product on reduction gives cis-2-benzyl-4-ethoxycarbonyl-1-methylpiperidine.Alternative routes to the latter were unsuccessful.The ketone (1a) was converted to several other 2,6-methano-1H-3-benzazonine derivatives of interest as potential analgesics. 2-Benzyl-4-ethoxycarbonyl-1-methylpiperidines give with methyllithium tertiary alcohols which cyclise (PPA) yielding 6,7-benzomorphans.
Bridged-ring Nitrogen Compounds. Part 5. Synthesis of 2,6-Methano-3-benzazonine ring-system
Proctor, George R.,Smith, Francis J.
, p. 1754 - 1762 (2007/10/02)
Syntheses of cis- and trans-4-benzyl- and 4-(3-methoxybenzyl)-2-methoxycarbonyl-1-methylpiperidines are described; amino-acids and amino-alcohols obtained from these compounds failed to cyclise. cis-2-Benzyl-4-ethoxycarbonyl-1-methylpiperidine has been ma
