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 C 24 H 23 N 3 O 3 and of the Corresponding Camphanic Acid Ester C 34 H 35 N 3 O 6

• 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: 01.07.1988
• ISSN: 0932-0776; 1865-7117
• DOI: 10.1515/znb-1988-0717

Abstract 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 24 H 23 N 3 O 3 (-)-3 and of the corresponding camphanic acid ester C 34 H 35 N 3 O 6 (-)-5 are orthorhombic and monoclinic with space groups P2 1 2 1 2 1 ((-)-3) and P2 1 ((-)-5). The respective cell parameters are a = 9.758(3), b = 12.815(2), c = 16.584(4) Å, Z = 4 and D x = 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, D x = 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.