159112-23-9Relevant articles and documents
Telescoped Continuous Flow Synthesis of Optically Active γ-Nitrobutyric Acids as Key Intermediates of Baclofen, Phenibut, and Fluorophenibut
?tv?s, Sándor B.,Kappe, C. Oliver,Llanes, Patricia,Pericàs, Miquel A.
, p. 8122 - 8126 (2020/11/03)
The two-step flow asymmetric synthesis of chiral γ-nitrobutyric acids as key intermediates of the GABA analogues baclofen, phenibut, and fluorophenibut is reported on a multigram scale. The telescoped process comprises an enantioselective Michael-type add
Water-compatible iminium activation: Organocatalytic Michael reactions of carbon-centered nucleophiles with enals
Palomo, Claudio,Landa, Aitor,Mielgo, Antonia,Oiarbide, Mikel,Puente, Angel,Vera, Silvia
, p. 8431 - 8435 (2008/09/19)
(Chemical Equation Presented) A pool of water-compatible catalysts, namely the chiral prolinol-based catalysts 1, has been developed for highly enantioselective C-C bond-forming Michael reactions in water (see scheme). The synthesis of (S)-Rolipram, a type IV phosphodiesterase inhibitor, was also demonstrated.
Potential GABAB Receptor Antagonists. VII. The Synthesis of 2-(4-Chlorophenyl)-3-nitropropan-1-amine and Related Analogues of Baclofen
Abbenante, Giovanni,Hughes, Robert,Prager, Rolf H.
, p. 1441 - 1452 (2007/10/02)
3-Nitro-2-phenylpropan-1-amine and 2-(4-chlorophenyl)-3-nitropropan-1-amine have been synthesized by the addition of nitrous acid to the corresponding trifluoroacetylaminomethylstyrenes followed by reduction of the double bond with sodium borohydride.A more general and efficient route involves the Michael addition of nitroalkane anions to methyl cinnamates followed by Curtius degradation of the corresponding acids. 2-(4-Chlorophenyl)-3-nitropropan-1-amine is a specific agonist of GABA and the GABAB receptor, with about half the activity of racemic baclofen at the isolated guinea pig ileum.Methylation or dimethylation at C3 decreases activity markedly.