Synthesis of the labeled D1 receptor antagonist SCH 23390 using [11C] carbon dioxide

A new synthesis is described for the production of the positron emitting radiopharmaceutical R-(+)-7-chloro-8-hydroxy-2,3,4,5-tetrahydro-3-N-[11C]methyl-1-phenyl-1H- 3-benzazepine (SCH 23390, 2a). This novel method involves reductive carboxylation, in which [11C]CO2 is reacted with the trimethylsily...

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Published in:Applied radiation and isotopes 1989, Vol.40 (5), p.425-427
Main Authors: SIYA RAM, EHRENKAUFER, R. E, SPICER, L. D
Format: Article
Language:English
Subjects:
Benzazepines - chemical synthesis
Carbon Dioxide
Carbon Radioisotopes
Chemistry
Dopamine Antagonists
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Isotope Labeling
Organic chemistry
Preparations and properties
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container_issue 5
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container_title Applied radiation and isotopes
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SPICER, L. D
description A new synthesis is described for the production of the positron emitting radiopharmaceutical R-(+)-7-chloro-8-hydroxy-2,3,4,5-tetrahydro-3-N-[11C]methyl-1-phenyl-1H- 3-benzazepine (SCH 23390, 2a). This novel method involves reductive carboxylation, in which [11C]CO2 is reacted with the trimethylsilyl derivative of the desmethyl compound (SCH 24518, 1a) followed by treatment with lithium aluminum hydride, to afford no carrier added 11C-labeled SCH 23390. The procedure gave chemically and radiochemically pure 11C-labeled SCH 23390 in 53-72% radiochemical yield with an unoptimized specific activity of 40 Ci/mmol within 45-50 min from the end of bombardment.
doi_str_mv 10.1016/0883-2889(89)90210-4
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source Backfile Package - Physics General (Legacy) [YPA]
subjects Benzazepines - chemical synthesis
Carbon Dioxide
Carbon Radioisotopes
Chemistry
Dopamine Antagonists
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Isotope Labeling
Organic chemistry
Preparations and properties
title Synthesis of the labeled D1 receptor antagonist SCH 23390 using [11C] carbon dioxide
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