Two-Step Iron(0)-Mediated N-Demethylation of N-Methyl Alkaloids
Publication type: Journal Article
Publication date: 2010-06-21
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
20565062
Organic Chemistry
Abstract
A mild and simple two-step Fe(0)-mediated N-demethylation of a number of tertiary N-methyl alkaloids is described. The tertiary N-methylamine is first oxidized to the corresponding N-oxide, which is isolated as the hydrochloride salt. Subsequent treatment of the N-oxide hydrochloride with iron powder readily provides the N-demethylated amine. Representative substrates include a number of opiate and tropane alkaloids. Key intermediates in the synthesis of semisynthetic 14-hydroxy pharmaceutical opiates such as oxycodone and oxymorphone are also readily N-demethylated using this method.
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Metrics
53
Total citations:
53
Citations from 2024:
4
(7.55%)
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MLA
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GOST
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Kok G. B. et al. Two-Step Iron(0)-Mediated N-Demethylation of N-Methyl Alkaloids // Journal of Organic Chemistry. 2010. Vol. 75. No. 14. pp. 4806-4811.
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Kok G. B., Pye C. C., Singer R. D., Scammells P. Two-Step Iron(0)-Mediated N-Demethylation of N-Methyl Alkaloids // Journal of Organic Chemistry. 2010. Vol. 75. No. 14. pp. 4806-4811.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/jo1008492
UR - https://doi.org/10.1021/jo1008492
TI - Two-Step Iron(0)-Mediated N-Demethylation of N-Methyl Alkaloids
T2 - Journal of Organic Chemistry
AU - Kok, Gaik B
AU - Pye, Cory C.
AU - Singer, Robert D.
AU - Scammells, Peter
PY - 2010
DA - 2010/06/21
PB - American Chemical Society (ACS)
SP - 4806-4811
IS - 14
VL - 75
PMID - 20565062
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2010_Kok,
author = {Gaik B Kok and Cory C. Pye and Robert D. Singer and Peter Scammells},
title = {Two-Step Iron(0)-Mediated N-Demethylation of N-Methyl Alkaloids},
journal = {Journal of Organic Chemistry},
year = {2010},
volume = {75},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/jo1008492},
number = {14},
pages = {4806--4811},
doi = {10.1021/jo1008492}
}
Cite this
MLA
Copy
Kok, Gaik B., et al. “Two-Step Iron(0)-Mediated N-Demethylation of N-Methyl Alkaloids.” Journal of Organic Chemistry, vol. 75, no. 14, Jun. 2010, pp. 4806-4811. https://doi.org/10.1021/jo1008492.