52950-37-5Relevant articles and documents
Divergent Synthesis of γ-Amino Acid and γ-Lactam Derivatives from meso-Glutaric Anhydrides
Connon, Stephen J.,Craig, Ryan,Smith, Simon N.
supporting information, p. 13378 - 13382 (2020/10/02)
The first divergent synthesis of both γ-amino acid and γ-lactam derivatives from meso-glutaric anhydrides is described. The organocatalytic desymmetrisation with TMSN3 relies on controlled generation of a nucleophilic ammonium azide species mediated by a polystyrene-bound base to promote efficient silylazidation. After Curtius rearrangement of the acyl azide intermediate to access the corresponding isocyanate, hydrolysis/alcoholysis provided uniformly high yields of γ-amino acids and their N-protected counterparts. The same intermediates were shown to undergo an unprecedented decarboxylation–cyclisation cascade in situ to provide synthetically useful yields of γ-lactam derivatives without using any further activating agents. Mechanistic insights invoke the intermediacy of an unconventional γ-N-carboxyanhydride (γ-NCA) in the latter process. Among the examples prepared using this transformation are 8 APIs/molecules of considerable medicinal interest.
Synthesis of Nonracemic Tetrazole GABA Analogs
Reznikov,Ostrovskii,Klimochkin, Yu. N.
, p. 1715 - 1721 (2019/02/14)
Nonracemic 3-substituted 4-(1H-tetrazol-1-yl)butanoic acids, analogs of the neurotropic drugs phenibut, tolibut, and baclofen, were synthesized by a three-component reaction of the R-isomers of the corresponding amino acids, triethyl orthoformate, and sod
A novel method for the synthesis of racemic pregabalin, baclofen and 3-phenibut involving lossen rearrangement
Ponnusamy, Kannan,Davis Presley,Nagapillai, Prakash,Deivanayagam, Eswaramoorthy
, p. 275 - 278 (2018/09/14)
Pregabalin,baclofen,and3-phenibutareγ-aminobutyricacid receptorsusedasanticonvulsant agents. The racemic forms of these anticonvulsants have been prepared by Lossen rearrangement. This procedure also provides an easy method to prepare carbamates useful intermediates to prepare anticonvulsants. This process is economical and easy to scale-up and yields are good.