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The Journal of organic chemistry

Development of a two-step route to 3-PBC and βCCt, two agents active against alcohol self-administration in rodent and primate models.


PMID 21495660

Abstract

To gain access to 3-propoxy-β-carboline hydrochloride (3-PBC·HCl) (1·HCl) and β-carboline-3-carboxylate-tert-butyl ester (βCCt) (2), potential clinical agents active against alcohol self-administration, a two-step route was developed. This process involves a palladium-catalyzed Buchwald-Hartwig coupling and an intramolecular Heck reaction. This two-step route provides rapid access to multigram quantities of 3-PBC (1) and βCCt (2), as well as analogues for studies of alcohol self-administration. The overall yield of 3-PBC (1) was improved from 8% to 50% by this route.

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SML0249
βCCt, ≥98% (HPLC)
C16H16N2O2