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Synthesis 2014; 46(04): 515-521
DOI: 10.1055/s-0033-1340462
DOI: 10.1055/s-0033-1340462
paper
An Efficient Synthesis of 4(5)-Benzyl-l-histidines Employing Catalytic Transfer Hydrogenolysis at Elevated Temperatures
Further Information
Publication History
Received: 15 October 2013
Accepted after revision: 21 November 2013
Publication Date:
10 December 2013 (online)
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.
Key words
amino acids - benzylation - Pictet–Spengler reaction - catalytic transfer hydrogenolysis - electrophilic aromatic substitutionSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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