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An Efficient Multigram Synthesis of the Potent Histamine H3 Antagonist GT-2331 and the Reassessment of the Absolute Configuration
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posted on 2004-01-09, 00:00 authored by Huaqing Liu, Francis A. Kerdesky, Lawrence A. Black, Michael Fitzgerald, Rodger Henry, Timothy A. Esbenshade, Arthur A. Hancock, Youssef L. BennaniGT-2331 is a potent histamine H3 antagonist
which has entered clinical trials. Efficient multigram syntheses of this compound and its enantiomer are described.
The literature reports that GT-2331 is the dextrorotatory
(+), more potent, enantiomer of 4-[2-(5,5-dimethylhex-1-ynyl)cyclopropyl]-1H-imidazole with the absolute configuration of (1R,2R)-1. However, we found that the dextrorotatory, more potent, enantiomer of 4-[2-(5,5-dimethylhex-1-ynyl)cyclopropyl]-1H-imidazole has the (1S,2S) absolute
configuration. We suggest a reconsideration of the absolute
configuration of GT-2331.