A. Novak, M. Štefanič, Uroš Grošelj
Feb 1, 2014
Citations
0
Influential Citations
3
Citations
Journal
Helvetica Chimica Acta
Abstract
A simple five-step synthesis of fully substituted (4RS,5RS)-4-aminopyrazolidin-3-ones as analogs of D-cycloserine was developed. It comprises a two-step preparation of 5-substituted (4RS,5RS)-4-(benzyloxycarbonylamino)pyrazolidin-3-ones, reductive alkylation at N(1), alkylation of the amidic N(2) with alkyl halides, and simultaneous hydrogenolytic deprotection/reductive alkylation of the primary NH2 group. The synthesis enables an easy stepwise functionalization of the pyrazolidin-3-one core with only two types of common reagents, aldehydes (or ketones) and alkyl halides. The structures of products were elucidated by NMR spectroscopy and X-ray diffraction.