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A facile and efficient synthesis of 14 C‐labelled sulforaphane
Author(s) -
D'Souza Christopher A.,
Amin Shantu,
Desai Dhimant
Publication year - 2003
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.724
Subject(s) - chemistry , sulforaphane , isothiocyanate , nitrile , yield (engineering) , hydrogen peroxide , medicinal chemistry , amine gas treating , organic chemistry , nuclear chemistry , biochemistry , materials science , metallurgy
Abstract Isothiocyanates have gained considerable attention for their role as potent chemopreventive agents. Sulforaphane, 1a (SFN), a naturally occurring isothiocyanate, was isotopically labelled in five steps starting from 3‐(methylthio)‐1‐propanol ( 2 ) . Reacting 2 with tosyl chloride in the presence of Et 3 N yielded the tosylate 3 . Gently refluxing 3 with K 14 CN in DMF gave the nitrile 4b . Reduction to the amine 5b was achieved using BH 3 ‐THF. Oxidation with 30% hydrogen peroxide followed by treatment with thiophosgene yielded (±)[1‐ 14 C]SFN, 1b . The overall radiochemical yield was 4.4% based on the starting K 14 CN. Copyright © 2003 John Wiley & Sons, Ltd.