Tetrahedron letters

Synthesis and reactivity of pyrrolo [3, 2-e] indole: removal of a N-BOM group from an unactivated indole

JE Macor, JT Forman, RJ Post, K Ryan

Index: Macor, John E.; Forman, James T.; Post, Ronald J.; Ryan, Kevin Tetrahedron Letters, 1997 , vol. 38, # 10 p. 1673 - 1676

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Citation Number: 22

Abstract

A practical synthesis of pyrrolo [3, 2-e] indole (1) is described. Different hydrogenation conditions of the indol-4-ylacetonitrile (3) afforded either 1-BOM-pyrrolo [3, 2-e] indole (4, 42% from 5-nitroindole) or 1-hydroxymethylpyrrolo [3, 2-e] indole (5, 46% from 5- nitroindole). Removal of the benzyl group was found to be problematic, but could be accomplished in moderate yield. Treatment of the resulting 1-hydroxymethylpyrrolo [3, 2-e] ...