uu.seUppsala University Publications
Change search
Link to record
Permanent link

Direct link
BETA
Nordeman, Patrik, Docent
Publications (10 of 30) Show all publications
Gonzalez, M. A. C., Nordeman, P., Gomez, A. B., Meyer, D. N., Antoni, G., Schou, M. & Szabo, K. J. (2018). [18F]fluoro-benziodoxole: a no-carrier-added electrophilic fluorinating reagent. Rapid, simple radiosynthesis, purification and application for fluorine-18 labelling. Chemical Communications, 54(34), 4286-4289
Open this publication in new window or tab >>[18F]fluoro-benziodoxole: a no-carrier-added electrophilic fluorinating reagent. Rapid, simple radiosynthesis, purification and application for fluorine-18 labelling
Show others...
2018 (English)In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 54, no 34, p. 4286-4289Article in journal (Refereed) Published
Abstract [en]

Operationally simple radiosynthesis and purification of [F-18]fluoro-benziodoxole was developed starting from a cyclotron produced [F-18]F- precursor, [F-18]TBAF, and tosyl-benziodoxole. The synthetic utility of [F-18]fluoro-benziodoxole was demonstrated by electrophilic fluorocyclization of o-styrilamides proceeding with high RCC (typically 50-90%) and high molar activity (up to 396 GBq mol(-1)).

National Category
Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-354948 (URN)10.1039/c8cc00526e (DOI)000430935200013 ()29632936 (PubMedID)
Funder
VINNOVASwedish Research Council
Available from: 2018-06-25 Created: 2018-06-25 Last updated: 2018-06-25Bibliographically approved
Nordeman, P., Yngve, U., Wilking, H., Gustavsson, S. Å., Eriksson, J. & Antoni, G. (2018). Automated GMP-production of α-[11 C]methyl-L-tryptophan using a tracer production system (TPS). Journal of labelled compounds & radiopharmaceuticals, 61(14), 1106-1109
Open this publication in new window or tab >>Automated GMP-production of α-[11 C]methyl-L-tryptophan using a tracer production system (TPS)
Show others...
2018 (English)In: Journal of labelled compounds & radiopharmaceuticals, ISSN 0362-4803, E-ISSN 1099-1344, Vol. 61, no 14, p. 1106-1109Article in journal (Refereed) Published
Abstract [en]

The radiosynthesis and GMP validation of [11 C]AMT for human use are described. Three consecutive batches were produced giving 940-3790 MBq (4%-17% RCY, decay corrected, based on [11 C]CO2 ) of the tracer. The molar activity at the end of synthesis was 19 to 35 GBq/μmol, the radiochemical purity was ≥98%, and the enantiomeric purity was >99%. While the synthesis method was automated using a new generation of synthesis equipment, tracer production system developed in house, the method should be readily applicable to other synthesis platforms with minor modifications.

Keywords
[11C]AMT, automation, methyl iodide, positron emission tomography, tracer production system
National Category
Medicinal Chemistry
Identifiers
urn:nbn:se:uu:diva-368809 (URN)10.1002/jlcr.3648 (DOI)000453709100011 ()29902836 (PubMedID)
Available from: 2018-12-07 Created: 2018-12-07 Last updated: 2019-01-15Bibliographically approved
Odell, L. R., Åkerbladh, L., Schembri, L. S., Nordeman, P., Roslin, S. & Eriksson, J. (2018). Carbonylations beyond aryl-X: Development of new multicomponent reactions. Paper presented at 255th National Meeting and Exposition of the American-Chemical-Society (ACS) - Nexus of Food, Energy, and Water, MAR 18-22, 2018, New Orleans, LA. Abstract of Papers of the American Chemical Society, 255
Open this publication in new window or tab >>Carbonylations beyond aryl-X: Development of new multicomponent reactions
Show others...
2018 (English)In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 255Article in journal, Meeting abstract (Other academic) Published
National Category
Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-367232 (URN)000435539901514 ()
Conference
255th National Meeting and Exposition of the American-Chemical-Society (ACS) - Nexus of Food, Energy, and Water, MAR 18-22, 2018, New Orleans, LA
Available from: 2018-12-06 Created: 2018-12-06 Last updated: 2018-12-06Bibliographically approved
Roy, T., Rydfjord, J., Sävmarker, J. & Nordeman, P. (2018). Palladium-catalyzed carbonylation of aryl bromides using microwave heating and bis[CP-Fe(II)-(CO)2] as a carbon monoxide source. Tetrahedron Letters, 59(13), 1230-1232
Open this publication in new window or tab >>Palladium-catalyzed carbonylation of aryl bromides using microwave heating and bis[CP-Fe(II)-(CO)2] as a carbon monoxide source
2018 (English)In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 59, no 13, p. 1230-1232Article in journal (Refereed) Published
Abstract [en]

A palladium-catalyzed, microwave assisted carbonylative reaction is described for the synthesis of benzamides from aryl bromides and primary or secondary amines. The developed method uses bis(cyclopentadienyldicarbonyliron) as a solid source of carbon monoxide to produce a diverse set of secondary and tertiary amides in 42-82% yield.

Keywords
Palladium, Carbon monoxide, Carbonylation, CORM, Microwaves
National Category
Organic Chemistry
Research subject
Chemistry with specialization in Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-355077 (URN)10.1016/j.tetlet.2018.02.035 (DOI)000428007300015 ()
Available from: 2018-06-26 Created: 2018-06-26 Last updated: 2019-06-28Bibliographically approved
Roslin, S., Dahl, K. & Nordeman, P. (2018). Reaction of 11C‐benzoyl chlorides with metalloid reagents: 11C‐labeling of benzyl alcohols, benzaldehydes, and phenylketones from [11C]CO. Journal of Labelled Compounds and Radiopharmaceuticals, 61(5), 447-454
Open this publication in new window or tab >>Reaction of 11C‐benzoyl chlorides with metalloid reagents: 11C‐labeling of benzyl alcohols, benzaldehydes, and phenylketones from [11C]CO
2018 (English)In: Journal of Labelled Compounds and Radiopharmaceuticals, ISSN 0362-4803, Vol. 61, no 5, p. 447-454Article in journal (Refereed) Published
Abstract [en]

In this article, we describe the carbon‐11 (11C, t1/2 = 20.4 minutes) labeling of benzyl alcohols, benzaldehydes, and ketones using an efficient 2-€step synthesis in which 11C-€carbon monoxide is used in an initial palladium-€mediated reaction to produce 11C-€benzoyl chloride as a key intermediate. In the second step, the obtained 11C-€benzoyl chloride is further treated with a metalloid reagent to furnish the final 11C-€labeled product. Benzyl alcohols were obtained in moderated to high non‐isolated radiochemical yields (RCY, 35%-90%) with lithium aluminum hydride or lithium aluminum deuteride as metalloid reagent. Changing the metalloid reagent to either tributyltin hydride or sodium borohydride, allowed for the reliable syntheses of 11C-€benzaldehydes in RCYs ranging from 58% to 95%. Finally, sodium tetraphenylborate were utilized to obtain 11C-€phenyl ketones in high RCYs (77%-95%). The developed method provides a new and efficient route to 3 different classes of compounds starting from aryl iodides or aryl bromides.

Keywords
benzaldehydes, benzyl alcohols, carbon monoxide, carbon-€11, carbonylation, phenyl ketones
National Category
Medicinal Chemistry Organic Chemistry
Research subject
Chemistry with specialization in Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-355074 (URN)10.1002/jlcr.3609 (DOI)000431660100005 ()29377217 (PubMedID)
Available from: 2018-06-26 Created: 2018-06-26 Last updated: 2018-08-20Bibliographically approved
Dahl, K. & Nordeman, P. (2017). 11C-Acetylation of Amines with [11C]Methyl Iodide with Bis(cyclopentadienyldicarbonyliron) as the CO Source. European Journal of Organic Chemistry (38), 5785-5788
Open this publication in new window or tab >>11C-Acetylation of Amines with [11C]Methyl Iodide with Bis(cyclopentadienyldicarbonyliron) as the CO Source
2017 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 38, p. 5785-5788Article in journal (Refereed) Published
Abstract [en]

We describe herein a novel approach for the direct 11C-acetylation of amines. The carbonylative protocol is palladium-mediated, uses bis(cyclopentadienyldicarbonyliron) as the CO source, and [11C]methyl iodide or [11C]methyl iodide-D3 as a radioactive precursor. A set of functionalized primary and secondary amines was 11C-labelled in radiochemical yields ranging from 7–85 %. The potential use of this method for positron emission tomography radiotracer production was additionally demonstrated by the radiosynthesis of [11C]lacosamide, [11C]melatonine, and [11C]acecainide in 44–55 % RCY.

Keywords
Isotopic labeling, Acylation, Positron emission tomography, Palladium, Methyl iodide
National Category
Medicinal Chemistry Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-339752 (URN)10.1002/ejoc.201701154 (DOI)000413162300010 ()
Note

Title in WoS: C-11-Acetylation of Amines with [C-11]Methyl Iodide with Bis(cyclopentadienyldicarbonyliron) as the CO Source

Available from: 2018-01-25 Created: 2018-01-25 Last updated: 2018-02-21Bibliographically approved
Andersen, T. L., Nordeman, P., Christoffersen, H. F., Audrain, H., Antoni, G. & Skrydstrup, T. (2017). Application of Methyl Bisphosphine-Ligated Palladium Complexes for Low Pressure N-C-11-Acetylation of Peptides. Angewandte Chemie International Edition, 56(16), 4549-4553
Open this publication in new window or tab >>Application of Methyl Bisphosphine-Ligated Palladium Complexes for Low Pressure N-C-11-Acetylation of Peptides
Show others...
2017 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 56, no 16, p. 4549-4553Article in journal (Refereed) Published
Abstract [en]

A mild and effective method is described for C-11-labeling of peptides selectively at the N-terminal nitrogen or at internal lysine positions. The presented method relies on the use of specific biphosphine palladium-methyl complexes and their high reactivity towards amino-carbonylation of amine groups in the presence [C-11] carbon monoxide. The protocol facilitates the production of native N-C-11-acetylated peptides, without any structural modifications and has been applied to a selection of bioactive peptides.

Keywords
C-11-labeling, carbonylation, palladium, peptides
National Category
Chemical Sciences
Identifiers
urn:nbn:se:uu:diva-320628 (URN)10.1002/anie.201700446 (DOI)000398154000026 ()28301077 (PubMedID)
Funder
Danish National Research Foundation, DNRF118
Note

De 2 sista författarna delar sistaförfattarskapet.

Available from: 2017-08-14 Created: 2017-08-14 Last updated: 2017-08-14Bibliographically approved
Elgland, M., Nordeman, P., Fyrner, T., Antoni, G., Nilsson, K. P. & Konradsson, P. (2017). beta-Configured clickable [F-18] FDGs as novel F-18-fluoroglycosylation tools for PET. New Journal of Chemistry, 41(18), 10231-10236
Open this publication in new window or tab >>beta-Configured clickable [F-18] FDGs as novel F-18-fluoroglycosylation tools for PET
Show others...
2017 (English)In: New Journal of Chemistry, ISSN 1144-0546, E-ISSN 1369-9261, Vol. 41, no 18, p. 10231-10236Article in journal (Refereed) Published
Abstract [en]

In oncology and neurology the F-18-radiolabeled glucose analogue 2-deoxy-2-[F-18]fluoro-D-glucose ([F-18]FDG) is by far the most commonly employed metabolic imaging agent for positron emission tomography (PET). Herein, we report a novel synthetic route to beta-configured mannopyranoside precursors and a chemoselective F-18-fluoroglycosylation method that employ two b-configured [F-18]FDG derivatives equipped with either a terminal azide or alkyne aglycon respectively, for use as a CuAAC clickable tool set for PET. The b-configured precursors provided the corresponding [F-18]FDGs in a radiochemical yield of 77-88%. Further, the clickability of these [F-18]FDGs was investigated by click coupling to the suitably functionalized Fmoc-protected amino acids, Fmoc-N-(propargyl)-glycine and Fmoc-3-azido-L-alanine, which provided the F-18-fluoroglycosylated amino acid conjugates in radiochemical yields of 75-83%. The F-18-fluoroglycosylated amino acids presented herein constitute a new and interesting class of metabolic PET radiotracers.

Place, publisher, year, edition, pages
ROYAL SOC CHEMISTRY, 2017
National Category
Chemical Sciences
Identifiers
urn:nbn:se:uu:diva-336822 (URN)10.1039/c7nj00716g (DOI)000411767400073 ()
Funder
Swedish Foundation for Strategic Research Swedish Research Council
Available from: 2017-12-20 Created: 2017-12-20 Last updated: 2017-12-20Bibliographically approved
Dahl, K. & Nordeman, P. (2017). C-11-Carbonylation through in Situ Generated C-11-Benzoyl Chlorides with Tetrabutylammonium Chloride as Chloride Source. European Journal of Organic Chemistry (18), 2648-2651
Open this publication in new window or tab >>C-11-Carbonylation through in Situ Generated C-11-Benzoyl Chlorides with Tetrabutylammonium Chloride as Chloride Source
2017 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 18, p. 2648-2651Article in journal (Refereed) Published
Abstract [en]

Aromatic C-11-containing acids, amides, esters, and aldehydes were obtained through a novel C-11-carbonylative reaction. In the two-step process, aryl iodides are first reacted with (CO)-C-11 and tetrabutylammonium chloride in a palladium-mediated reaction to yield C-11-benzoyl chlorides in situ. The crude mixture is then further treated with either a hydroxide, amine, alcohol, or a hydride in a second vial to furnish the final C-11-carbonyl product. The monodentate ligand tri-tert-butylphosphonium tetrafluoroborate was proven to be crucial for obtaining high radiochemical yields (RCY). A wide range of C-11-containing carbonyl compounds were successfully radiolabeled in moderate to excellent RCYs, ranging from 41-93%. The synthetic retinoic acid tamibarotene was obtained in a RCY of 89%, whereas the Boc-protected procainamide was labelled in 68% RCY, which is a significantly increase (2-3 fold) in RCY compared to other published methods.

Place, publisher, year, edition, pages
WILEY-V C H VERLAG GMBH, 2017
Keywords
Isotopes, Carbonylation, Positron emission tomography, Benzoyl chlorides, Palladium
National Category
Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-325330 (URN)10.1002/ejoc.201700268 (DOI)000401434900015 ()
Available from: 2017-07-03 Created: 2017-07-03 Last updated: 2017-07-03Bibliographically approved
Nordeman, P., Chow, S. Y., Odell, A. F., Antoni, G. & Odell, L. R. (2017). Palladium-mediated C-11-carbonylations using aryl halides and cyanamide. Organic and biomolecular chemistry, 15(22), 4875-4881
Open this publication in new window or tab >>Palladium-mediated C-11-carbonylations using aryl halides and cyanamide
Show others...
2017 (English)In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 15, no 22, p. 4875-4881Article in journal (Refereed) Published
Abstract [en]

A robust and high-yielding radiochemical synthesis of C-11-N-cyanobenzamides using a palladium-mediated aminocarbonylation with C-11-CO, aryl halides and cyanamide is described. The bidentate ligand 1,1'-bis(diphenylphosphino)ferrocene provided C-11-N-cyanobenzamides from aryl-iodides, bromides, triflates and even chlorides in 28-79% radiochemical yield after semi-preparative HPLC. To further highlight the utility of this method, novel C-11-N-cyanobenzamide analogs of flufenamic acid, meflanamic acid, dazoxiben and tamibarotene were synthesized in 34-71% radiochemical yields.

National Category
Medicinal Chemistry
Identifiers
urn:nbn:se:uu:diva-327370 (URN)10.1039/c7ob01064h (DOI)000403005500018 ()28537303 (PubMedID)
Available from: 2017-08-11 Created: 2017-08-11 Last updated: 2018-01-13Bibliographically approved
Organisations

Search in DiVA

Show all publications