Research Article

One-step reductive etherification of 4-[18F]fluoro-benzaldehyde with decaborane

  1. Uta Funke,
  2. Hongmei Jia†,
  3. Steffen Fischer,
  4. Matthias Scheunemann*,
  5. Jörg Steinbach‡

Article first published online: 11 JUL 2006

DOI: 10.1002/jlcr.1087

Issue

Journal of Labelled Compounds and Radiopharmaceuticals

Journal of Labelled Compounds and Radiopharmaceuticals

Volume 49, Issue 9, pages 745–755, August 2006

Additional Information

How to Cite

Funke, U., Jia, H., Fischer, S., Scheunemann, M. and Steinbach, J. (2006), One-step reductive etherification of 4-[18F]fluoro-benzaldehyde with decaborane. Journal of Labelled Compounds and Radiopharmaceuticals, 49: 745–755. doi: 10.1002/jlcr.1087

Author Information

  1. Institute of Interdisciplinary Isotope Research, Permoserstraβe 15, 04318 Leipzig, Germany

  1. †

    Beijing Normal University, College of Chemistry, Beijing 100875, People's Republic of China.

  2. ‡

    Forschungszentrum Rossendorf, Institute of Radiopharmacy, POB 510119, 01314 Dresden, Germany.

*Institute of Interdisciplinary Isotope Research, Permoserstraße 15, 04318 Leipzig, Germany

Publication History

  1. Issue published online: 13 JUL 2006
  2. Article first published online: 11 JUL 2006
  3. Manuscript Revised: 29 APR 2006
  4. Manuscript Accepted: 29 APR 2006
  5. Manuscript Received: 14 MAR 2006

Funded by

  • China Scholarship Council

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Keywords:

  • 4-[18F]fluoro-benzylether;
  • fluorine-18;
  • reductive etherification;
  • decaborane;
  • labelling

Abstract

Reductive coupling reactions between 4-[18F]fluoro-benzaldehyde ([18F]1) and different alcohols by use of decaborane (B10H14) as reducing agent have the potential to synthesize 4-[18F]fluoro-benzylethers in one step. [18F]1 was synthesized from 4-trimethylammonium benzaldehyde (triflate salt) via a standard fluorination procedure (K[18F]F/Kryptofix® 222) in dimethylformamide at 90°C for 25 min and purified by solid-phase extraction. Subsequently, reductive etherifications of [18F]1 were performed as one-step reactions with primary and secondary alcohols, mediated by B10H14 in acetonitrile at 60°C. Various 4-[18F]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.

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