Synthesis of (R)-(-)-2-fluoronorapomorphine - A precursor for the synthesis of (R)-(-)-2-fluoro-N-[C]propylnorapomorphine for evaluation as a dopamine D agonist ligand for PET investigations

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Standard

Synthesis of (R)-(-)-2-fluoronorapomorphine - A precursor for the synthesis of (R)-(-)-2-fluoro-N-[C]propylnorapomorphine for evaluation as a dopamine D agonist ligand for PET investigations. / Søndergaard, Kåre; Kristensen, Jesper Langgaard; Gillings, Nic; Begtrup, M.

I: European Journal of Organic Chemistry, Nr. 20, 14.10.2005, s. 4428-4433.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Søndergaard, K, Kristensen, JL, Gillings, N & Begtrup, M 2005, 'Synthesis of (R)-(-)-2-fluoronorapomorphine - A precursor for the synthesis of (R)-(-)-2-fluoro-N-[C]propylnorapomorphine for evaluation as a dopamine D agonist ligand for PET investigations', European Journal of Organic Chemistry, nr. 20, s. 4428-4433. https://doi.org/10.1002/ejoc.200500295

APA

Søndergaard, K., Kristensen, J. L., Gillings, N., & Begtrup, M. (2005). Synthesis of (R)-(-)-2-fluoronorapomorphine - A precursor for the synthesis of (R)-(-)-2-fluoro-N-[C]propylnorapomorphine for evaluation as a dopamine D agonist ligand for PET investigations. European Journal of Organic Chemistry, (20), 4428-4433. https://doi.org/10.1002/ejoc.200500295

Vancouver

Søndergaard K, Kristensen JL, Gillings N, Begtrup M. Synthesis of (R)-(-)-2-fluoronorapomorphine - A precursor for the synthesis of (R)-(-)-2-fluoro-N-[C]propylnorapomorphine for evaluation as a dopamine D agonist ligand for PET investigations. European Journal of Organic Chemistry. 2005 okt. 14;(20):4428-4433. https://doi.org/10.1002/ejoc.200500295

Author

Søndergaard, Kåre ; Kristensen, Jesper Langgaard ; Gillings, Nic ; Begtrup, M. / Synthesis of (R)-(-)-2-fluoronorapomorphine - A precursor for the synthesis of (R)-(-)-2-fluoro-N-[C]propylnorapomorphine for evaluation as a dopamine D agonist ligand for PET investigations. I: European Journal of Organic Chemistry. 2005 ; Nr. 20. s. 4428-4433.

Bibtex

@article{7dfe365001854294b82a604388e5f4db,
title = "Synthesis of (R)-(-)-2-fluoronorapomorphine - A precursor for the synthesis of (R)-(-)-2-fluoro-N-[C]propylnorapomorphine for evaluation as a dopamine D agonist ligand for PET investigations",
abstract = "2-Fluoronorapomorphine, the PET labelling precursor to 2-fluoro-N-[ C]propylnorapomorphine, was prepared in 13 steps from codeine in a total yield of 10 %. Codeine was converted in four steps into N-benzylnorcodeine which was oxidised by using the Swern protocol. Subseguent acid-catalysed rearrangement afforded N-benzylnormorphothebaine which was selectively triflylated at the 2-position and pivaloylated at the 11-position. The triflate underwent palladium-catalysed amination with benzophenone imine. Amination conditions required sequential base addition to give substantial conversion of the triflate to the corresponding N-substituted benzophenone imine. After acidic hydrolysis the resulting aniline was transformed into the 2-fluoro compound via the Balz-Schiemann reaction. Hydrogenolysis of the N-benzyl group followed by deprotection of the catechol moiety using BBr provided 2-fluoronorapomorphine.",
author = "K{\aa}re S{\o}ndergaard and Kristensen, {Jesper Langgaard} and Nic Gillings and M. Begtrup",
year = "2005",
month = oct,
day = "14",
doi = "10.1002/ejoc.200500295",
language = "English",
pages = "4428--4433",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",
number = "20",

}

RIS

TY - JOUR

T1 - Synthesis of (R)-(-)-2-fluoronorapomorphine - A precursor for the synthesis of (R)-(-)-2-fluoro-N-[C]propylnorapomorphine for evaluation as a dopamine D agonist ligand for PET investigations

AU - Søndergaard, Kåre

AU - Kristensen, Jesper Langgaard

AU - Gillings, Nic

AU - Begtrup, M.

PY - 2005/10/14

Y1 - 2005/10/14

N2 - 2-Fluoronorapomorphine, the PET labelling precursor to 2-fluoro-N-[ C]propylnorapomorphine, was prepared in 13 steps from codeine in a total yield of 10 %. Codeine was converted in four steps into N-benzylnorcodeine which was oxidised by using the Swern protocol. Subseguent acid-catalysed rearrangement afforded N-benzylnormorphothebaine which was selectively triflylated at the 2-position and pivaloylated at the 11-position. The triflate underwent palladium-catalysed amination with benzophenone imine. Amination conditions required sequential base addition to give substantial conversion of the triflate to the corresponding N-substituted benzophenone imine. After acidic hydrolysis the resulting aniline was transformed into the 2-fluoro compound via the Balz-Schiemann reaction. Hydrogenolysis of the N-benzyl group followed by deprotection of the catechol moiety using BBr provided 2-fluoronorapomorphine.

AB - 2-Fluoronorapomorphine, the PET labelling precursor to 2-fluoro-N-[ C]propylnorapomorphine, was prepared in 13 steps from codeine in a total yield of 10 %. Codeine was converted in four steps into N-benzylnorcodeine which was oxidised by using the Swern protocol. Subseguent acid-catalysed rearrangement afforded N-benzylnormorphothebaine which was selectively triflylated at the 2-position and pivaloylated at the 11-position. The triflate underwent palladium-catalysed amination with benzophenone imine. Amination conditions required sequential base addition to give substantial conversion of the triflate to the corresponding N-substituted benzophenone imine. After acidic hydrolysis the resulting aniline was transformed into the 2-fluoro compound via the Balz-Schiemann reaction. Hydrogenolysis of the N-benzyl group followed by deprotection of the catechol moiety using BBr provided 2-fluoronorapomorphine.

UR - http://www.scopus.com/inward/record.url?scp=27144453646&partnerID=8YFLogxK

U2 - 10.1002/ejoc.200500295

DO - 10.1002/ejoc.200500295

M3 - Journal article

AN - SCOPUS:27144453646

SP - 4428

EP - 4433

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 20

ER -

ID: 45438091