Ly. Gong et H. Parnes, SYNTHESIS OF THE H-3 LABELED 5-HT3 ANTAGONIST (RS-25259-197) AT HIGH SPECIFIC ACTIVITY, Journal of labelled compounds & radiopharmaceuticals, 38(5), 1996, pp. 425-433
Citations number
6
Categorie Soggetti
Chemistry Analytical","Pharmacology & Pharmacy","Biochemical Research Methods
The preparation of the title compound, a selective 5-HT3 antagonist wi
th anti-emetic properties, is described. The key intermediate involved
is 6-bromo-1,2-dihydronaphthoic acid ((5) under bar), which was synth
esized from 4-bromophenylacetic acid by Micheal addition, acid-induced
ring cyclization, reduction and dehydration. Compound ((5) under bar)
was selected because it has two labelling sites to ensure high specif
ic activity of the final product. Reduction of amide (6) under bar wit
h carrier-free tritium gas, followed by reduction of the amide functio
nal group with BF3-OEt(2) and intramolecular cyclization furnished the
title compound having a specific activity of 70.4 Ci/mmol and >99% pu
rity.