Synthesis and crystal structure of (S)-pindolol |
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Authors: | Alexander A Bredikhin Zemfira A Bredikhina Alexey V Kurenkov Dmitry B Krivolapov |
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Institution: | A.E. Arbuzov Institute of Organic & Physical Chemistry, Kazan Scientific Centre of the Russian Academy of Sciences, Kazan 420088 Russian Federation |
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Abstract: | Racemic 3-(4-indolyloxy)-1,2-propanediol 2 has been effectively resolved into (S)- and (R)-enantiomers by a preferential crystallization procedure. Non-racemic (S)-2 was converted into (S)-4-(2,3-epoxypropoxy)-1H-indole (S)-4 via a Mitsunobu reaction and then into (S)-pindolol (S)-1. The crystalline (S)-1 was studied by single crystal X-ray diffraction. A large number of symmetry independent molecules (Z′ = 6) led to a weakening of the system of strong intermolecular hydrogen bonds, which combined with a loose packing (PI = 64.6%), may be the cause of the abnormally low melting point of (S)-1 as compared with rac-1. |
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Keywords: | Corresponding author Tel : +7 843 2727393 fax: +7 843 2731872 |
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