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Article

Darstellung und Atropisomerie von 1-[2-(2,2-Dimethylpiperidino)phenyl]ethanol

by
H. Möhrle
*,§ and
M. Jeandrée
Institut für Pharmazeutische Chemie der Heinrich-Heine-Universität, Universitätsstr. 1, 0-40225 Düsseldorf
*
Author to whom correspondence should be addressed.
§
Herrn Univ.-Prof. Dr. W. Wendelin zum 60. Geburtstag gewidmet
Sci. Pharm. 2001, 69(1), 1-10; https://doi.org/10.3797/scipharm.aut-01-01
Submission received: 23 August 2000 / Accepted: 23 November 2000 / Published: 30 March 2001
Versions Notes

Abstract

The title compound was prepared by Hg(II)-edta dehydrogenation of the aminoalkohol 2 via the benzoxazine 4, which reacted with methylmagnesiumiodide to 6. This compound shows in the NMR spectrum atropisomerism for the restricted rotation of the piperidine moiety about the aryl-C-N bond. The dehydrogenation of 6 stopped after a two electron withdrawal generating the benzoxazine 7, because the angular hydrogen atom occupies an equatorial position, which prevents stereoelectronic conditions for a further oxidation.
Keywords: Hg(II)-edta dehydrogenation; intramolecular aminoalkylation; pyrido[1,2-a][3,1]benzoxazine Hg(II)-edta dehydrogenation; intramolecular aminoalkylation; pyrido[1,2-a][3,1]benzoxazine

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MDPI and ACS Style

Möhrle, H.; Jeandrée, M. Darstellung und Atropisomerie von 1-[2-(2,2-Dimethylpiperidino)phenyl]ethanol. Sci. Pharm. 2001, 69, 1-10. https://doi.org/10.3797/scipharm.aut-01-01

AMA Style

Möhrle H, Jeandrée M. Darstellung und Atropisomerie von 1-[2-(2,2-Dimethylpiperidino)phenyl]ethanol. Scientia Pharmaceutica. 2001; 69(1):1-10. https://doi.org/10.3797/scipharm.aut-01-01

Chicago/Turabian Style

Möhrle, H., and M. Jeandrée. 2001. "Darstellung und Atropisomerie von 1-[2-(2,2-Dimethylpiperidino)phenyl]ethanol" Scientia Pharmaceutica 69, no. 1: 1-10. https://doi.org/10.3797/scipharm.aut-01-01

APA Style

Möhrle, H., & Jeandrée, M. (2001). Darstellung und Atropisomerie von 1-[2-(2,2-Dimethylpiperidino)phenyl]ethanol. Scientia Pharmaceutica, 69(1), 1-10. https://doi.org/10.3797/scipharm.aut-01-01

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