Hydrogen iodide-promoted reduction of beta-chlorovinamidinium salts

IW Davies; M Taylor; D Hughes; PJ Reider

doi:10.1021/ol006497z

Hydrogen iodide-promoted reduction of beta-chlorovinamidinium salts

Org Lett. 2000 Oct 19;2(21):3385-7. doi: 10.1021/ol006497z.

Authors

IW Davies¹, M Taylor, D Hughes, PJ Reider

Affiliation

¹ Department of Process Research, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, USA.

PMID: 11029217
DOI: 10.1021/ol006497z

Abstract

HI cleanly reduced chlorovinamidinium salts to the vinamidinium salt in essentially quantitative assay yield and 55-85% isolated yield following recrystallization. The reaction proceeds via protonation of the beta-carbon atom of the vinamidinium and dechlorination via the formation of I-Cl.