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Synthesis 1997; 1997(4): 443-449
DOI: 10.1055/s-1997-1214
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A Direct Synthesis of 3-(Pyrrolidin-3-yl)indoles for Use As Conformationally Restricted Analogs of Tryptamines

John E. Macor* , David H. Blank, Kevin Ryan, Ronald J. Post
  • *Department of Medicinal Chemistry, Central Research Division, Pfizer Inc, Groton, Connecticut 06340, USA
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Publication Date:
31 December 2000 (online)

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An efficient, two step synthesis of 3-(pyrrolidin-3-yl)indoles 4 is described. Indoles react with maleimides in refluxing acetic acid affording 3-(indol-3-yl)succinimides 6. Reaction times and yields depend on the substituents on the indole 5. Direct reduction of the succinimides 6 with LAH affords the desired conformationally restricted tryptamine derivatives 4.

3-(pyrrolidin-3-yl)indoles - tryptamines - 3-(indol-3-yl)succinimides