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Synthesis of (S)-cyano(3-phenoxyphenyl)methyl (1R,3R)- 3-[(1Z)-2-chloro-3,3,3-trifluoro-1-propenyl]-2,2-dimethylcyclopropanecarboxylate-1-14C

✍ Scribed by Peter L. Johnson

Publisher
John Wiley and Sons
Year
2007
Tongue
French
Weight
122 KB
Volume
50
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

γ‐Cyhalothrin (1a), (S)‐cyano(3‐phenoxyphenyl)methyl (1__R__,3__R__)‐3‐[(1__Z__)‐2‐chloro‐3,3,3‐trifluoro‐1‐propenyl]‐2,2‐dimethylcyclopropanecarboxylate, is a single‐isomer, synthetic pyrethroid insecticide marketed by Pytech Chemicals GmbH, a joint venture between Dow AgroSciences and Cheminova A/S. As a part of the registration process there was a need to incorporate a carbon‐14 label into the cyclopropyl ring of this molecule. A high yielding radiochemical synthesis of γ‐cyhalothrin was developed from readily available carbon‐14 labeled N‐t‐Boc protected glycine. This seven step synthesis, followed by a preparative normal phase HPLC separation of diastereomers, provided 21.8 mCi of γ‐cyhalothrin‐1‐^14^C (1b) with >98% radiochemical purity. Copyright © 2007 John Wiley & Sons, Ltd.

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