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Synthesis of (3RS)- and (3SR)-acetoxy-(3aRS,8bSR)-N-acetyl-5-methoxy-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indoles

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Abstract

Stereoisomeric 3-acetoxy-5-methoxy-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indoles differing by the configuration of the C3 atom were synthesized. The reaction of N-acetyl-6-(cyclopent-2-en-1-yl)-2-methoxyaniline with 50% hydrogen peroxide in the presence of Na2WO4-H3PO4 in AcOH gave (3RS,3aRS,8bSR)-N-acetyl-3-hydroxy-5-methoxy-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole which was converted into the corresponding 3-O-acetyl derivative by treatment with acetic anhydride in pyridine. N-Acetyl-6-(cyclopent-2-en-1-yl)-2-methoxyaniline reacted with iodine in methylene chloride in the presence of NaHCO3 to produce (3SR,3aRS,8bSR)-3-acetoxy-5-methoxy-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole which was subjected to acetylation at the nitrogen atom by reaction with acetic anhydride. The structure of (3RS,3aRS,8bSR)-N-acetyl-3-hydroxy-5-methyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole was proved by X-ray analysis.

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Authors and Affiliations

  1. Affiliate of Ufa State Petrotechnical University, ul. Gubkina 67, Salavat, 453250, Bashkortostan, Russia

    N. A. Likhacheva

  2. Nesmeyanov Institute of Organometallic Compounds, Russian Academy of Sciences, Moscow, Russia

    A. A. Korlyukov

  3. Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054, Bashkortostan, Russia

    R. R. Gataullin

Authors
  1. N. A. Likhacheva
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  2. A. A. Korlyukov
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  3. R. R. Gataullin
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Correspondence to N. A. Likhacheva.

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Original Russian Text © N.A. Likhacheva, A.A. Korlyukov, R.R. Gataullin, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 3, pp. 406–409.

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Likhacheva, N.A., Korlyukov, A.A. & Gataullin, R.R. Synthesis of (3RS)- and (3SR)-acetoxy-(3aRS,8bSR)-N-acetyl-5-methoxy-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indoles. Russ J Org Chem 45, 394–398 (2009). https://doi.org/10.1134/S1070428009030075

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  • DOI: https://doi.org/10.1134/S1070428009030075

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