Fluorine-18 labeled 1-amino-3-fluorocyclobutane-1-carboxylic acid (FACBC), a new tumor-avid amino acid, was synthesized for positron emission tomography. [18F]FACBC was prepared with high specific activity by nucleophilic displacement with an overall radiochemical yield of 12% (EOB). Synthesis of the triflate precursor was accomplished in nine steps starting from the reaction of benzyl bromide with epichlorohydrin which gave 1-chloro-2-benzyloxy-3-brompropane. A key step involves conversion of 3-benzyloxy-cyclobutane-1,1-dicarboxylate diamide to a mixture of diastereomeric 2-benzyloxycyclobutane hydantoins.
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Shoup et al. (1999) studied this question.
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