From [(11)C]CO2 to [(11)C]amides: a rapid one-pot synthesis via the Mitsunobu reaction

S Bongarzone; A Runser; C Taddei; A K Haji Dheere; A D Gee

doi:10.1039/c7cc01407d

From [(11)C]CO2 to [(11)C]amides: a rapid one-pot synthesis via the Mitsunobu reaction

S Bongarzone, A Runser, C Taddei, A K Haji Dheere, A D Gee

King's College London

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Abstract

A novel amide synthesis methodology is described using amines, CO2 and Grignard reagents and Mitsunobu reagents. The method was applied to carbon-11 radiochemistry to label amides using cyclotron-produced [(11)C]CO2. The synthetic utility of the one-pot labelling methodology was demonstrated by producing [(11)C]melatonin. The incorporation of [(11)C]CO2 into [(11)C]melatonin was 36% - determined by radioHPLC 2 min post [(11)C]CO2 delivery.

Original language	English
Pages (from-to)	5334-5337
Number of pages	4
Journal	Chemical communications (Cambridge, England)
Volume	53
Issue number	38
Early online date	27 Apr 2017
DOIs	https://doi.org/10.1039/c7cc01407d
Publication status	E-pub ahead of print - 27 Apr 2017

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From [(11)C]CO2 to [(11)C]amides_BONGARZONE_Publishedonline27April2017_GOLD VoR (CC BY)Final published version, 1.66 MBLicence: CC BY

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abstract = "A novel amide synthesis methodology is described using amines, CO2 and Grignard reagents and Mitsunobu reagents. The method was applied to carbon-11 radiochemistry to label amides using cyclotron-produced [(11)C]CO2. The synthetic utility of the one-pot labelling methodology was demonstrated by producing [(11)C]melatonin. The incorporation of [(11)C]CO2 into [(11)C]melatonin was 36% - determined by radioHPLC 2 min post [(11)C]CO2 delivery.",

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AU - Bongarzone, S

AU - Runser, A

AU - Taddei, C

AU - Dheere, A K Haji

AU - Gee, A D

PY - 2017/4/27

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N2 - A novel amide synthesis methodology is described using amines, CO2 and Grignard reagents and Mitsunobu reagents. The method was applied to carbon-11 radiochemistry to label amides using cyclotron-produced [(11)C]CO2. The synthetic utility of the one-pot labelling methodology was demonstrated by producing [(11)C]melatonin. The incorporation of [(11)C]CO2 into [(11)C]melatonin was 36% - determined by radioHPLC 2 min post [(11)C]CO2 delivery.

AB - A novel amide synthesis methodology is described using amines, CO2 and Grignard reagents and Mitsunobu reagents. The method was applied to carbon-11 radiochemistry to label amides using cyclotron-produced [(11)C]CO2. The synthetic utility of the one-pot labelling methodology was demonstrated by producing [(11)C]melatonin. The incorporation of [(11)C]CO2 into [(11)C]melatonin was 36% - determined by radioHPLC 2 min post [(11)C]CO2 delivery.

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DO - 10.1039/c7cc01407d

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JF - Chemical communications (Cambridge, England)

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ER -

From [(11)C]CO2 to [(11)C]amides: a rapid one-pot synthesis via the Mitsunobu reaction

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