ChemInformVolume 21, Issue 39 Preparative Organic Chemistry ChemInform Abstract: N-Fluorolactams: Rapid, Mild, and Regiospecific Fluorinating Agents. N. SATYAMURTHY, N. SATYAMURTHY Div. Nuclear Med. Biophys., Dep. Radiol. Sci., UCLA School Med., Lab. Nuclear Med., Los Angeles, CA 90024, USASearch for more papers by this authorG. T. BIDA, G. T. BIDA Div. Nuclear Med. Biophys., Dep. Radiol. Sci., UCLA School Med., Lab. Nuclear Med., Los Angeles, CA 90024, USASearch for more papers by this authorM. E. PHELPS, M. E. PHELPS Div. Nuclear Med. Biophys., Dep. Radiol. Sci., UCLA School Med., Lab. Nuclear Med., Los Angeles, CA 90024, USASearch for more papers by this authorJ. R. BARRIO, J. R. BARRIO Div. Nuclear Med. Biophys., Dep. Radiol. Sci., UCLA School Med., Lab. Nuclear Med., Los Angeles, CA 90024, USASearch for more papers by this author N. SATYAMURTHY, N. SATYAMURTHY Div. Nuclear Med. Biophys., Dep. Radiol. Sci., UCLA School Med., Lab. Nuclear Med., Los Angeles, CA 90024, USASearch for more papers by this authorG. T. BIDA, G. T. BIDA Div. Nuclear Med. Biophys., Dep. Radiol. Sci., UCLA School Med., Lab. Nuclear Med., Los Angeles, CA 90024, USASearch for more papers by this authorM. E. PHELPS, M. E. PHELPS Div. Nuclear Med. Biophys., Dep. Radiol. Sci., UCLA School Med., Lab. Nuclear Med., Los Angeles, CA 90024, USASearch for more papers by this authorJ. R. BARRIO, J. R. BARRIO Div. Nuclear Med. Biophys., Dep. Radiol. Sci., UCLA School Med., Lab. Nuclear Med., Los Angeles, CA 90024, USASearch for more papers by this author First published: September 25, 1990 https://doi.org/10.1002/chin.199039108Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume21, Issue39September 25, 1990 RelatedInformation

N-[18F]fluoro-N-alkylsulfonamides were synthesized by the fluorination of secondary sulfonamides with [18F]F2. Radiochemical yields up to 45% (out of a maximum possible yield of 50%) for these reactions have been realized. The N-[18F]fluorosulfonamides rapidly and regiospecifically fluorinate a variety of Grignard reagents and aryllithium under very mild conditions to give 18F-labeled derivatives in good yields.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTN-Fluoro lactams: rapid, mild, and regiospecific fluorinating agentsN. Satyamurthy, Gerald T. Bida, Michael E. Phelps, and Jorge R. BarrioCite this: J. Org. Chem. 1990, 55, 10, 3373–3374Publication Date (Print):May 1, 1990Publication History Published online1 May 2002Published inissue 1 May 1990https://pubs.acs.org/doi/10.1021/jo00297a071https://doi.org/10.1021/jo00297a071research-articleACS PublicationsRequest reuse permissionsArticle Views438Altmetric-Citations24LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

The synthesis of 3-(2'-[18F]fluoroethyl)spiperone (1c), a radiotracer useful for imaging the brain dopamine receptor system in vivo using positron emission tomography, is described. Precursors of 1c, the functional 3-N-alkyl derivatives of spiperone (4), were prepared by the alkylation of the amide group in spiperone (2a) by 1,2-disubstituted ethanes under phase transfer conditions. A comprehensive evaluation of the reaction of the derivatives 4a-h with no-carrier-added K18F/Kryptofix clearly indicated that the ketalized derivatives 4e-h were the choice of the precursors for 1c. The i.r., MS and NMR spectral data suggested that under phase transfer reaction conditions, the amide nitrogen was preferentially alkylated. To provide a firm basis for comparison with related analogues, an x-ray analysis was performed on a single crystal of 3-(2'-fluoroethyl)spiperone (1d). The tomographic behavior of 1c in human brain tissue was measured for more than 7 h and was consistent with the labeling of dopamine D-2 receptors.

Phenols have been synthesized in excellent yields using a cation exchange resin (H+ form) assisted decomposition of 1-aryl-3,3-dialkyltriazanes in the presence of water. This method is also amenable to a high yield and high enrichment synthesis of oxygen-17 and 18 labeled phenols.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTAcid-catalyzed thermal decomposition of 1-aryl-3,3-dialkyltriazenes in the presence of nucleophilesN. Satyamurthy, Jorge R. Barrio, Derrick G. Schmidt, Craig Kammerer, Gerald T. Bida, and Michael E. PhelpsCite this: J. Org. Chem. 1990, 55, 15, 4560–4564Publication Date (Print):July 1, 1990Publication History Published online1 May 2002Published inissue 1 July 1990https://pubs.acs.org/doi/10.1021/jo00302a018https://doi.org/10.1021/jo00302a018research-articleACS PublicationsRequest reuse permissionsArticle Views704Altmetric-Citations43LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

Regioselective radiofluorodemercuration of the 6-mercurio derivative 5 with [18F]acetylhypofluorite afforded, after acidic hydrolysis, 6-[18F]fluoro-L-3,4-dihydroxyphenylalanine (6-FD, 1) with a radiochemical yield of 11% (decay corrected and based on the total amount of [18F]F2 recovered from the target). 6-FD was obtained with a chemical and radiochemical purity of greater than 99% and with a level of mercury in the final preparation of less than 20 ppb. Utilization of a remote, semiautomated production system, resulted in the preparation of a sterile, pyrogen-free product suitable for human injection after a synthesis time of 50 min.

A computer-controlled general purpose chemistry process control unit (CPCU) suitable for the automated production of radiochemicals has been developed. This valve-and-tubing synthesis system can be user programmed to accommodate a variety of chemical processes. In a practical demonstration of its utility, the CPCU has been configured and programmed to synthesize 2-deoxy-2-[18F]fluoro-d-glucose (2-[18F]FDG) using aqueous [18F]fluoride ion. Using this instrument, the yield of 2-[18F]FDG from [18F]fluoride ion is 54.9% (± 11.2%, n = 125) corrected to EOB, after a synthesis time of 50–55 min. The average total activity produced (for runs of 5–10 μA) is 28.1 mCi/μA (± 5.03 mCi/μA). Thus, the amount of 2-[18F]FDG produced from a 10 μA for 1 h bombardment was 154.3 mCi (± 27.4 mCi). The unit has been similarly configured and programmed to synthesize 2-deoxy-2-[18F]fluoro-d-mannose (48% EOB), 3-(2′-[18F]fluoroethyl)spiperone (29% EOB), and [18F]fluoroacetate (66% EOB) from aqueous [18F]fluoride ion, and 2-[18F]FDG from gaseous acetyl hypo[18F]fluorite (20% EOB).

Journal of Labelled Compounds and RadiopharmaceuticalsVolume 26, Issue 1-12 p. 388-390 Symposium Abstract 18F-labeled benzamide derivatives: Synthesis of 3,5-dichloro-N-[1-{2-[18F]-fluoroethyl}-2-pyrrolidinyl)methyl]-6-methoxysalicylamide And derivatives as dopamine D-2 receptor-binding radioligands N. Satyamurthy, N. Satyamurthy UCLA School of Medicine, Division of Nuclear Medicine and Biophysics, Los Angeles, CA 90024Search for more papers by this authorJ.R. Barrio, J.R. Barrio UCLA School of Medicine, Division of Nuclear Medicine and Biophysics, Los Angeles, CA 90024Search for more papers by this authorG.T. Bida, G.T. Bida UCLA School of Medicine, Division of Nuclear Medicine and Biophysics, Los Angeles, CA 90024Search for more papers by this authorM.E. Phelps, M.E. Phelps UCLA School of Medicine, Division of Nuclear Medicine and Biophysics, Los Angeles, CA 90024Search for more papers by this author N. Satyamurthy, N. Satyamurthy UCLA School of Medicine, Division of Nuclear Medicine and Biophysics, Los Angeles, CA 90024Search for more papers by this authorJ.R. Barrio, J.R. Barrio UCLA School of Medicine, Division of Nuclear Medicine and Biophysics, Los Angeles, CA 90024Search for more papers by this authorG.T. Bida, G.T. Bida UCLA School of Medicine, Division of Nuclear Medicine and Biophysics, Los Angeles, CA 90024Search for more papers by this authorM.E. Phelps, M.E. Phelps UCLA School of Medicine, Division of Nuclear Medicine and Biophysics, Los Angeles, CA 90024Search for more papers by this author First published: January 1989 https://doi.org/10.1002/jlcr.25802601166Citations: 3AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat Citing Literature Volume26, Issue1-12January 1989Pages 388-390 RelatedInformation

Electrophilic fluorination of diazepam with elemental fluorine or gas phase acetyl hypofluorite gave 3-fluorodiazepam in 20–60% yields. Nucleophilic displacement of chlorine in 3-chlorodiazepam by fluoride ion also gave 3-fluorodiazepam in modest yields (maximum: 21%). Both of these methods were used for the synthesis of 18F-labelled 3-fluorodiazepam.

No-carrier-added (NCA)3-(2′-[18F]fluoroethyl)spiperone (5), a new dopamine receptor-binding radiopharmaceutical for positron emission tomography, was synthesized by two different methods. Alkylation of the amide nitrogen in spiperone by NCA [18F]fluorobromoethane in the presence of a strong base gave 5 (Method A). Experimental methods were also developed for the syntheses of functional 3-N-alkylderivatives of spiperone such as 3-(2′-bromoethyl)- or 3-(2′-methylsulfonyloxyethyl)spiperone (4a and 4b, respectively). These derivatives (4) reacted with NCA Ag18F, Cs18F or K18F/Kryptofix 222 in acetonitrile or DMSO to give 5 (Method B). Method B, using K18F/Kryptofix 222 in acetonitrile provided 5 in multimillicure amounts (30–40% isolated radiochemical yield) with a specific activity of 2–10/μmol (EOS) in less than 60 min. This one-step, one-pot synthesis is simple, and the high radiochemical yield of 5, as well as the 110 min half-life of 18F, permit multiple tomographic studies a day with one preparation. Tomographic results in monkey brain with 5 are consistent with the labeling of dopamine-D2 receptor systems.

AbstractDie Fluorierung der Glucale (I) führt mit von den Reaktionsbedingungen abhängigen Ausbeuten zu den 2‐Fluorhexosen (II) und (III).

The reaction of methyl 4,6-O-benzylidene-3-O-benzyl-2-O-trifluoromethanesulfonyl-beta-D- glucopyranoside in acetonitrile at 75 degrees C for 30 min with [18F]tetra-n-butylammonium fluoride, followed by silica gel column chromatographic purification, gave the corresponding [18F]methyl 4,6-O-benzylidene-3-O-benzyl-2-fluoro-beta-D-mannopyranoside with complete regio- and stereoselectivity (42% radiochemical yield). Hydrolysis of the radiolabeled fluoromannopyranoside intermediate with either 6 N HCl or 50% methanesulfonic acid for 30 min at 120 degrees C, followed by purification by column chromatography (ion retardation resin and neutral alumina), gave pure [18F]2-deoxy-2-fluoro-D-mannose ([18F]2-FDM) with an overall radiochemical yield (from [18F]fluoride ion) of 34%. Extension of this methodology to the no carrier added (nca) synthesis under phase transfer conditions (Kryptofix 222/K 18F/acetonitrile) gave nca [18F]2-FDM in a radiochemical yield of 75%. Purity and identity of the fluorinated products were confirmed by 1H and 19F NMR spectroscopy. The synthetic procedure described here permits for the first time the routine preparation of large amounts of [18F]2-FDM for tomographic studies.