Synthesis and X-Ray Analysis of the (S) Enantiomer of Methyl 5-Hydroxy-3,11-di-2-pyridyl-4,5-dihydro-1H,3H-2,6-methano- 6-benz[c]azocinecarboxylate C24H23N3O3 and of the Corresponding Camphanic Acid Ester C34H35N3O6
2014
Hesse, K.-F. | Holzgrabe, U. (Ulrike) | Piening, Barthold
Methyl 5-hydroxy-3,11-di-2-pyridyl-4,5-dihydro-1H,3H-2,6-methano-6-benz[c]azocinecarb-oxylate (-)-3 is synthesized by oxidative cyclization of an N-benzyl-4-piperidone, reduction and resolution with (-)-camphanic acid chloride.The structures of C₂₄H₂₃N₃O₃ (-)-3 and of the corresponding camphanic acid ester C₃₄H₃₅N₃O₆ (-)-5 are orthorhombic and monoclinic with space groups P2₁2₁2₁ ((-)-3) and P2₁ ((-)-5). The respective cell parameters are a = 9.758(3), b = 12.815(2), c = 16.584(4) Å, Z = 4 and Dₓ = 1.29 g cm⁻³ ((-)-3) and a = 11.189(1), b = 10.591(1), c -12.84(1) Å, β = 92.53(1)°, Z = 2, Dₓ = 1.27 g cm⁻³ ((-)-5). They were refined to R (unweighed) -0.037 ((-)-3), 0.069 ((-)-5) and R (weighed) = 0.035 ((-)-3), 0.061 ((-)-5) using 965, 1722 non-equivalent reflections, respectively. The absolute configuration of (-)-3 was determined as 2S, 3R. 5R, 6R, 11 R.
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