Efficient Regioselective Ring Opening of Activated Aziridine‐2‐Carboxylates with [18F]Fluoride

ChemistryOpen

Christina Schjoeth-Eskesen¹  Dr. Paul Robert Hansen²  Prof.𠁝r. Andreas Kjaer¹ 

[1] Department of Clinical Physiology, Nuclear Medicine & PET, Copenhagen University Hospital Rigshospitalet, Blegdamsvej 9, 2100 Copenhagen Ø (Denmark);Department of Drug Design & Pharmacology, University of Copenhagen, Universitetsparken 2, 2100 Copenhagen Ø (Denmark)

关键词: aziridines;    fluorine-18;    radiochemistry;    regioselectivity;    ring opening;   

DOI  :  10.1002/open.201402081

来源: Wiley

【 摘 要 】

Abstract

Aziridines can undergo a range of ring-opening reactions with nucleophiles. The regio- and stereochemistry of the products depend on the substituents on the aziridine. Aziridine ring-opening reactions have rarely been used in radiosynthesis. Herein we report the ring opening of activated aziridine-2-carboxylates with [¹⁸F]fluoride. The aziridine was activated for nucleophilic attack by substitution of various groups on the aziridine nitrogen atom. Fluorine-18 radiolabelling was followed by ester hydrolysis and removal of the activation group. Totally regioselective ring opening and subsequent deprotection was achieved with tert-butyloxycarbonyl- and carboxybenzyl-activated aziridines to give α-[¹⁸F]fluoro-β-alanine in good radiochemical yield.

【 授权许可】

CC BY-NC-ND   
© 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

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