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One‐step reductive etherification of 4‐[ 18 F]fluoro‐benzaldehyde with decaborane
Author(s) -
Funke Uta,
Jia Hongmei,
Fischer Steffen,
Scheunemann Matthias,
Steinbach Jörg
Publication year - 2006
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.1087
Subject(s) - benzaldehyde , decaborane , chemistry , trifluoromethanesulfonate , acetonitrile , dimethylformamide , coupling reaction , organic chemistry , medicinal chemistry , catalysis , solvent , boron
Reductive coupling reactions between 4‐[ 18 F]fluoro‐benzaldehyde ([ 18 F] 1 ) and different alcohols by use of decaborane (B 10 H 14 ) as reducing agent have the potential to synthesize 4‐[ 18 F]fluoro‐benzylethers in one step. [ 18 F] 1 was synthesized from 4‐trimethylammonium benzaldehyde (triflate salt) via a standard fluorination procedure (K[ 18 F]F/Kryptofix ® 222) in dimethylformamide at 90°C for 25 min and purified by solid‐phase extraction. Subsequently, reductive etherifications of [ 18 F] 1 were performed as one‐step reactions with primary and secondary alcohols, mediated by B 10 H 14 in acetonitrile at 60°C. Various 4‐[ 18 F]fluorobenzyl ethers (6 examples are shown) were obtained within 1–2 h reaction time in decay‐corrected radiochemical yields of 12–45%. Copyright © 2006 John Wiley & Sons, Ltd.