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The synthesis of the 14C and 2H-isotopomers of (R)-N-[2-(2′-ethoxyphenoxy)-ethyl]-N-2-[3-(4′-methoxy-3′-sulfonamido)-phenyl]-propylamine hydrochloride, an α1-adrenoreceptor antagonist

✍ Scribed by William J. Wheeler; Klaus K. Schmiegel; David C. Hunden

Publisher
John Wiley and Sons
Year
1989
Tongue
French
Weight
552 KB
Volume
27
Category
Article
ISSN
0022-2135

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✦ Synopsis

The synthesis of [14C]-and [2H]-labeled LY253351 (YM12617-I), a potent a,-receptor antagonist, which is potentially useful in the treatment of benign prostatic hypertrophy (BPH) is described. The [14C]-isotopomer was synthesized from [14C]-potassium cyanide in nine steps in 1.5% radiochemical yield. One of the key intermediates, [14C]-4-methoxyphenylacetone, was synthesized from [14C]-4-methoxyphenylacetyl chloride by a Pd(0)-catalyzed reaction with tetramethylstannane. The [2H]-labeled material was synthesized by a Pd/C catalyzed reductive amination with deuterium gas.

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