172879-74-2

Upstream product

• 172879-73-1 ethyl (S)-3,4-dihydro-5-methylthio-2H-pyrrole-2-carboxylate 
• 7149-65-7 ethyl (S)-pyroglutamate 
• 80442-95-1 ethyl (2S)-5-thioxo-3,4-dihydro-5H-pyrrole-2-carboxylate 

Downstream Products

• 435274-88-7 (2S,5S)-5-Cyano-pyrrolidine-2-carboxylic acid ethyl ester 
• 435274-89-8 (2S,5R)-5-Cyano-pyrrolidine-2-carboxylic acid ethyl ester 
• 468096-98-2 ethyl (3S,5aS)-tetrahydropyrrolo[1,2-b]oxaziridine-3-carboxylate 
• 468096-97-1 ethyl (3S,5aR)-tetrahydropyrrolo[1,2-b]oxaziridine-3-carboxylate 
• 81702-31-0 (2S,5S)-pyrrolidine-2,5-dicarboxylic acid 

Relevant academic research and scientific papers

Synthesis of (S)-3,4-Dihydro-2-pivaloyloxymethyl-2H-pyrrole 1-Oxide

The synthesis of a series of new enantiopure 3,4-dihydro-2H-pyrrole derivatives including the title nitrone and its cycloaddition product to dimethyl acetylenedicarboxylate is described.

Efficient synthesis of (S)-3,4-dihydro-2-pivaloyloxymethyl-2H-pyrrole 1-oxide

A convenient synthesis of the title nitrone is reported. The sequence starts from ethyl L-pyroglutamate as the source of chirality and the key step is the generation of an unstable α-methoxy-N-carboxylate ion, which readily decomposes to an imine. The oxidation of the imine with methyl(trifluoromethyl)dioxirane provides the enantiopure nitrone, which is trapped with dimethyl acetylenedicarboxylate.

An efficient synthesis of substituted prolines by the selective reduction and reductive cyanation of 2-pyrrolidones

Substituted pyrrolidones undergo selective reduction using Cp2ZrHCl (Schwartz's reagent) to form Δ1-pyrrolines, which can be isolated or directly cyanated and hydrolyzed to the corresponding proline. Short syntheses of glutamic semialdehyde (ethyl ester), the marine metabolite (2S,5S)-pyrrolidine-2,5-dicarboxylic acid, and the conformationally constrained amino acid 5,5-dimethylproline, are reported.