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Die Trimethylsilylierung von Indolyl-Verbindungen unter milden Reaktionsbedingungen

Trimethylsilylation of indolylic compounds under mild reaction conditions

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Summary

The1N-trimethylsilation rate of the indole nucleus by N-methyl-N-TMS-trifluoroacetamid (MSTFA) is increased by basic catalysts, whereas the commonly used trimethylchlorsilane (TMSCI) decreases the reaction rate. TMS-imidazol proved to be the most effective catalyst. The1N-trimethylsilation of N, N-diethyl-tryptamine, tryptamine, serotonine, trpytophan etc. is complete at 60 °C within 5 minutes.

Zusammenfassung

Basische Katalysatoren beschleunigen die1N-Trimethylsilylierung des Indolkerns mit N-Methyl-N-TMS-trifluoracetamid (MSTFA), wohingegen das üblicherweise benutzte Trimethylchlorsilan (TMSCI) die Reaktionsgeschwindigkeit herabsetzt. Als wirksamster Katalysator erwies sich N-Trimethylsilyl-imidazol, unter dessen Einfluß die1N-Trimethylsilylierung von N, N-Diäthyltryptamin, Tryptamin, Serotonin, Tryptophan etc. bei 60 °C innerhalb von 5 Minuten abgeschlossen ist.

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Abbreviations

TMS:

Trimethylsilyl

GC:

Gas-Chromatograph

MS:

Massenspektrometer

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Authors and Affiliations

  1. Institut für Biochemie der Universität Köln, An der Bottmühle 2, D-5, Köln 1, Bundesrepublik Deutschland

    M. Donike

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  1. M. Donike
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Additional information

Herrn Professor Dr.L. Birkofer zum 65. Geburtstag

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Donike, M. Die Trimethylsilylierung von Indolyl-Verbindungen unter milden Reaktionsbedingungen. Chromatographia 9, 440–442 (1976). https://doi.org/10.1007/BF02270732

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  • DOI: https://doi.org/10.1007/BF02270732

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