Synthesis of 1-Boc-3-fluoroazetidine-3-carboxylic Acid

…, JW Thuring, G Macdonald, N De Kimpe

Index: Van Hende, Eva; Verniest, Guido; Deroose, Frederik; Thuring, Jan-Willem; Macdonald, Gregor; De Kimpe, Norbert Journal of Organic Chemistry, 2009 , vol. 74, # 5 p. 2250 - 2253

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Citation Number: 15

Abstract

Synthetic strategies toward 3-fluoroazetidine-3-carboxylic acid, a new cyclic fluorinated β- amino acid with high potential as building block in medicinal chemistry, were evaluated. The successful pathway includes the bromofluorination of N-(diphenylmethylidene)-2-(4- methoxyphenoxymethyl)-2-propenylamine, yielding 1-diphenylmethyl-3-hydroxymethyl-3- fluoroazetidine after reduction of the imino bond, ring closure, and removal of the 4- ...