93713-33-8

Upstream product

• 90290-04-3 trans-N-benzyl-2,5-bis(ethoxycarbonyl)pyrrolidine 
• 72219-10-4 trans-N-benzylpyrrolidine-2,5-dicarbonitrile 
• 93713-34-9 (2R,5R)-1-Benzyl-pyrrolidine-2,5-dicarboxylic acid; compound with 2-amino-1-(4-nitro-phenyl)-propane-1,3-diol 

Downstream Products

• 136175-17-2 (2S,5S)-5-[(3S,5S)-1-Acetyl-5-(4-nitro-phenoxycarbonyl)-pyrrolidin-3-ylsulfanylmethyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 120980-88-3 trans-1-(tert-Butoxycarboxyl)-2(S)-(methoxycarbonyl)-5(S)-<(tosyloxy)methyl>pyrrolidine 
• 118396-01-3 (-)-(2S,5S)-N-benzyl-trans-2,5-bis(methoxycarbonyl)pyrrolidine 
• 93713-35-0 (2R,5R)-2,5-Pyrrolidinedicarboxylic acid 
• 93713-36-1 1-Benzyl-[(2R,5R)-2,5-bis(hydroxymethyl)]pyrrolidine 
• 93713-34-9 (2R,5R)-1-Benzyl-pyrrolidine-2,5-dicarboxylic acid; compound with 2-amino-1-(4-nitro-phenyl)-propane-1,3-diol 

Relevant academic research and scientific papers

Enantioselective biotransformations of racemic and meso pyrrolidine-2,5-dicarboxamides and their application in organic synthesis

In this paper, we report the amidase-catalyzed hydrolysis of pyrrolidine-2,5-dicarboxamides and their application in organic synthesis. Catalyzed by Rhodococcus erythropolis AJ270, an amidase containing microbial whole cell catalyst, racemic trans-pyrrolidine-2,5-carboxamide was kinetically resolved into (2S,5S)-pyrrolidine-2,5-dicarboxamide and (2R,5R)-5- carbamoylpyrrolidine-2-carboxylic acid in high yields and excellent enantioselectivity. Biocatalytic desymmetrization of meso cis- pyrrolidinedicarboxamide afforded enantiomerically pure (2R,5S)-5- carbamoylpyrrolidine-2-carboxylic acid in an almost quantitative yield. In both kinetic resolution and desymmetrization, the amidase always exhibited excellent 2R-enantioselectivity, although its catalytic efficiency was influenced dramatically by the steric effect of the substituent on the nitrogen atom of pyrrolidine ring. The synthetic potential of biotransformation was demonstrated by the scalable preparation of (2R,5R)- and (2R,5S)-5-carbamoylpyrrolidine-2- carboxylic acids and their conversions to aza-nucleoside analogues and druglike pyrroline-fused diazepin-11(5H)-one compounds.

Studies of N-Terminal Templates for α-Helix Formation. Synthesis and Conformational Analysis of (2S,5S,8S,11S)-1-Acetyl-1,4-diaza-3-keto-5-carboxy-10-thiatricyclo4,8>tridecane (Ac-Hel1-OH)

A convergent synthesis of the title compound, a conformationally restricted analogue of acetyl-L-prolyl-L-proline, from 1-acetyl-2(S)-carboxy-4(S)-mercaptopyrrolidine and trans-1-(tert-butoxycarbonyl)-2(S)-(methoxycarbonyl)-5(S)-pyrrolidine (Ac-Hel1-OH) is reported, along with a synthesis of (2S,8S,11S)-1-acetyl-1,4-diaza-3-keto-10-thiatricyclo4,8>tridecane.In the crystal and in CDCl3 solution the conformation of Ac-Hel1-OH is shown to approximate a staggered orientation at the 8,9-CC bond and an s-cis orientation at the acetyl amide bond.In DMF, DMSO, MeCN, and D2O significant amounts of the s-trans conformer are also present.

ASYMMETRIC ALKYLATION OF CARBOXYAMIDES BY USING trans-2,5-DISUBSTITUTED PYRROLIDINES AS CHIRAL AUXILIARIES

trans-2,5-Bis(methoxymethyl)- and trans-2,5-bis(methoxymethoxymethyl)pyrrolidines proved to be excellent chiral auxiliaries for the asymmetric alkylation of the corresponding carboxyamide enolates giving good chemical yield and high stereoselectivity (invariably over 95percent de), with remarkable flexibility to substrates and reaction conditions.