Issue 16, 2009
From the journal:

Organic & Biomolecular Chemistry

A new approach towards 1-phenyl and 1-benzyl substituted 2-(aminomethyl)cyclopropanecarboxamides as novel derivatives of the antidepressantMilnacipran†

Karel Vervisch,a   Matthias D'hooghe,a   Karl W. Törnroosb  and  Norbert De Kimpe*a  

* Corresponding authors

a Dep. of Organic Chemistry, Fac. of Bioscience Engineering, Ghent University, Coupure Links 653, Ghent, Belgium
E-mail: norbert.dekimpe@UGent.be
Fax: +32 9 264.62.43
Tel: +32 9 264.59.51

b Dep. of Chemistry, University of Bergen, Allégt, 41, Bergen, Norway

Abstract

2-(2-Cyano-2-phenylethyl)aziridines were converted into novel trans-2-aminomethyl-1-phenylcyclopropanecarboxamides via regiospecific ring opening and 3-exo-tet cyclisation, thus providing the first convenient entry into the trans-isomer of Milnacipran as a useful template for further derivatisation. Furthermore, unprecedented 2-aminomethyl-1-benzylcyclopropanecarboxamides have been synthesized using two different routes starting from 2-(2-cyanoethyl)aziridines, both involving α-benzylation with respect to the nitrile group and aziridine to cyclopropane ring transformation.

Graphical abstract: A new approach towards 1-phenyl and 1-benzyl substituted 2-(aminomethyl)cyclopropanecarboxamides as novel derivatives of the antidepressant Milnacipran

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/B904611A
Article type
Paper
Submitted
05 Mar 2009
Accepted
02 Jun 2009
First published
30 Jun 2009

Org. Biomol. Chem., 2009,7, 3271-3279

Permissions

Request permissions

A new approach towards 1-phenyl and 1-benzyl substituted 2-(aminomethyl)cyclopropanecarboxamides as novel derivatives of the antidepressant Milnacipran

K. Vervisch, M. D'hooghe, K. W. Törnroos and N. De Kimpe, Org. Biomol. Chem., 2009, 7, 3271 DOI: 10.1039/B904611A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements