An efficient synthesis of 4(5)-benzyl- L -histidines employing catalytic transfer hydrogenolysis at elevated temperatures

D. David Smith, Audrey T. Gallagher, Vincent M. Crowley, Wayne M. Gergens, Peter W. Abel, Martin Hulce

Research output: Contribution to journalArticle

2 Scopus citations

Abstract

An efficient two-step synthesis of 4(5)-benzyl-l-histidine from l-histidine was developed. A Pictet-Spengler reaction between l-histidine and benzaldehyde in the presence of excess strong base yielded 4-l-phenylspinacine within one hour. Catalytic transfer hydrogenolysis in methanol at reflux using ammonium formate rapidly converted 4-l-phenylspinacine to 4(5)-benzyl-l-histidine within five minutes. No racemization of the final product 4(5)-benzyl-l-histidine was observed using the Marfey reagent. To show the utility of this method, a series of fluorinated benzylhistidines were prepared.

Original languageEnglish (US)
Article numberSS-2013-M0680-OP
Pages (from-to)515-521
Number of pages7
JournalSynthesis (Germany)
Volume46
Issue number4
DOIs
StatePublished - Feb 1 2014

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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