The Journal of Organic Chemistry

Convenient synthesis of 4-methylhistamine and racemic. alpha., 4-dimethylhistamine and. alpha., 4-dimethylhistidine

DD Davey, WC Lumma Jr

Index: Davey, D. D.; Lumma, W. C. Journal of Organic Chemistry, 1989 , vol. 54, # 13 p. 3211 - 3213

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Citation Number: 11

Abstract

We have previously described the preparation of 4 from commercially available 5-methyl-1H- imidazole-4-carboxylic acid ethyl ester in 71% isolated yield.'A published procedure for the reduction of 4 to the alcohol 5 with lithium aluminum hydridee (LAH) resulted in unacceptable yields of 20-30%. The low yields obtained for this reaction appear to result from hydride addition to the 4, 5-double bond, followed by further reduction of the ...