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

• Published in: Zeitschrift für Naturforschung. B, A journal of chemical sciences Vol. 43; no. 7; pp. 901 - 910
• Main Authors: Hesse, K.-F., Holzgrabe, Ulrike, Piening, Barthold
• Format: Journal Article
• Language: English
• Published: Tübingen Verlag der Zeitschrift für Naturforschung 01.07.1988
• Subjects: 5-Hydroxy-4,5-dihydro-2,6-methano-2-benzazocine; Chemistry; Condensed matter: structure, mechanical and thermal properties; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Organic chemistry; Organic compounds; Physics; Preparations and properties; Resolution; Structure of solids and liquids; crystallography; Structure of specific crystalline solids; Synthesis; X-Ray; Cyclization; Molecular structure; Nitrogen heterocycle; Six membered ring; Aromatic compound; Oxidation; Experimental study; X ray diffraction; Organic compounds; Enantiomer(-); Crystalline structure
• DOI: 10.1515/znb-1988-0717
• ISSN: 0932-0776

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 C (-)-3 and of the corresponding camphanic acid ester C (-)-5 are orthorhombic and monoclinic with space groups P2 ((-)-3) and P2 ((-)-5). The respective cell parameters are a = 9.758(3), b = 12.815(2), c = 16.584(4) Å, Z = 4 and D = 1.29 g cm ((-)-3) and a = 11.189(1), b = 10.591(1), c -12.84(1) Å, β = 92.53(1)°, Z = 2, D = 1.27 g cm ((-)-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.