Abstract
(1R,3S)-2-Benzyl-3-methoxycarbonyl-1-methylcarboxymethyl-1,2,3,4-tetrahydro-9H-pyrido [3,4-b] indole, C23H24N2O4, was synthesized by a modified Pictet-Spengler reaction, and its crystal and molecular structure determined by single crystal X-ray diffraction methods. The crystals are monoclinic:P21 (No. 4),a=11.336(1),b=8.919(1),c=10.314(1)Å,β=100.81(1)°,Z=2. The structure has been solved by direct methods, and refined toR=0.041 for 2203 observed reflections. The six-membered heterocyclic ring is in a half-chair conformation, and the substituents at C(3) and C(5) occupy axial and equatorial positions respectively. The CH2Ph group attached to N(4) is in the generally less favoured axial position. The nitrogen atom of the indole system forms an intermolecular hydrogen bond with the carbonyl oxygen of the CH2CO2 Me group, the N⋯O distance being 2.995(3)Å.
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Everett, J.H., Reynolds, C.D., Sparks, C.A. et al. Crystal and molecular structure of aN(2)-benzyl-1,3-disubstituted-1,2,3,4-tetrahydro-β-carboline. Journal of Crystallographic and Spectroscopic Research 20, 109–115 (1990). https://doi.org/10.1007/BF01160961
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DOI: https://doi.org/10.1007/BF01160961