102508-03-2

Usage

Type of isomer

cis-

Structure

2,5-Pyrrolidinedicarboxylic acid with a 1-(phenylmethyl) group and dimethyl ester

Usage

Intermediate in the synthesis of pharmaceuticals

Potential applications

Development of drugs for central nervous system disorders and as a chiral building block in organic synthesis

Safety precautions

Handle with care and follow safety protocols to avoid health and environmental hazards

Upstream product

• 868-72-4 dimethyl rac-2,5-dibromohexanedioate 
• 100-46-9 benzylamine 
• 868-72-4 dimethyl 2,5-dibromohexanedioate 
• 51483-87-5 1-Benzyl-2,5-pyrrolidindicarbonsaeure-dimethylester 
• 124-04-9 Adipic acid 
• 868-72-4 dimethyl (2R,5S)-2,5-dibromohexanedioate 
• 29548-86-5 2,5-dibromohexanedioyl dichloride 
• 111-50-2 Adipic acid dichloride 

Downstream Products

• 102572-59-8 (2S,5R)-N-benzyl-5-methoxycarbonylproline 
• 51483-83-1 (2R,5S)-1-Benzyl-pyrrolidine-2,5-dicarboxylic acid monomethyl ester 
• 116836-61-4 trans-1-Benzyl-2,5-pyrrolidindicarbonsaeure-dimethylester 
• 281668-36-8 meso-1-benzyl-2,5-bis(methoxycarbonyl)-2,5-dimethylpyrrolidine 
• 157008-40-7 trans-N-benzyl-2,5-bis(hydroxymethyl)pyrrolidine 
• 111138-50-2 (2S,5S)-1-Benzyl-pyrrolidine-2,5-dicarboxylic acid monomethyl ester 
• 727351-54-4 rac-(2S,5R)-5-fluoro-2-piperidinecarboxylic acid 

Relevant academic research and scientific papers

Methyl N-[(2R,5S)-1-N-benzyl-5-methoxycarbonylprolyl]-(S)-phenylalaninate

In order to prepare new chiral auxiliaries useful in developing a new method of synthesis of optically pure amines or β-amino acids, an unsymmetric derivative of pyrrolidine has been obtained, methyl 2-[(2R,5S)-(1-benzyl-5-methoxypyrrolidin-2-yl)carbonyl-(S)-amino]-3- phenylpropanoate, C24H28N2O5. This has been crystallized and subjected to X-ray analysis in order to ascertain the absolute configuration of the two asymmetric C atoms of the ring. The five-membered ring is half-chair shaped. An intramolecular hydrogen bond links the amino N atom of the phenylalanine group to the carbonyl of the 5-methoxycarbonyl group.

A mechanochemical approach to access the proline-proline diketopiperazine framework

Ball milling was exploited to prepare a substituted proline building block by mechanochemical nucleophilic substitution. Subsequently, the mechanocoupling of hindered proline amino acid derivatives was developed to provide proline-proline dipeptides under solvent-free conditions. A deprotection-cyclization sequence yielded the corresponding diketopiperazines that were obtained with a high stereoselectivity which could be explained by DFT calculations. Using this method, an enantiopure disubstituted Pro-Pro diketopiperazine was synthesized in 4 steps, making 5 new bonds using a ball mill.

Switching and Conformational Fixation of Amides Through Proximate Positive Charges

Tertiary amides, which usually occur as cis/trans mixtures, can be effectively shifted to the cis conformation by placing a positive charge in close proximity to the amide carbonyl. This effect was used to prepare cis-configured prolyl amides and to facilitate a strongly rotamer-dependent radical cyclization. Taking charge of conformation: Tertiary amides, which usually occur as cis/trans mixtures, can be effectively shifted to the cis conformation by placing a positive charge in close proximity to the amide carbonyl. This effect was used to prepare cis-configured prolyl amides and to facilitate a strongly rotamer-dependent radical cyclization.

Synthesis of a conformationally rigid analogue of 2-aminoadipic acid containing an 8-azabicyclo[3.2.1]octane skeleton

A new, conformationally rigid analogue of 2-aminoadipic acid, 8-[(benzyloxy)carbonyl]-3-methylene-8-azabicyclo[3.2.1]octane-1,5-dicarboxylic acid, is synthesized from dimethyl rac-2,5-dibromohexanedioate. The key steps involve alkylation-cyclization of 1-

Synthesis of 7-azabicyclo[2.2.1]heptane-1,4-dicarboxylic acid, a rigid non-chiral analogue of 2-aminoadipic acid

A non-chiral, rigid 7-azabicyclo[2.2.1]heptane-1,4-dicarboxylic acid, an analogue of 2-aminoadipic acid, has been synthesized in six steps from dimethyl-meso-2,5-dibromohexanedioate in 28% total yield. A key step in the synthesis is double alkylation of a

HIV protease inhibitors

Combinatorial libraries of HIV and FIV protease inhibitors are characterized by alpha-keto amide or hydroxyethylamine core structures flanked by on one side by substituted pyrrolidines, piperidines, or azasugars and on the other side by phenylalanine, tyrosine, or substituted tyrosines. The libraries are synthesized via a one step coupling reaction. Highly efficacious drug candidates are identified by screening the libraries for binding and inhibitory activity against both HIV and FIV protease. Drug candidates displaying clinically useful activity against both HIV and FIV protease are identified as being potentially resistive against a loss of inhibitory activity due to development of resistant strains of HIV.

Pyrrolidinopiperazinedione as chiral auxillary and its use in asymmetric Mannich synthesis

Functionalised diketopiperazines (DKPs) are easily obtained optically pure by disymmetrization of a mesopyrrolidine and can be easily converted to an α-amino amine containing compound. As a first example, one of the new chiral auxiliaries has been used to prepare an optically pure β-amino ester through a Mannich reaction.

Synthesis of both enantiomers of C2 symmetric trans-2,5- bis(hydroxymethyl)pyrrolidine. Lipase mediated sequential kinetic resolutions

Lipase mediated sequential kinetic resolution has been employed to give both enantiomers of trans-2,5-bis(hydroxymethyl)pyrrolidine in optically pure form. The effect of different parameters on the ee and yields in these resolutions are also reported.

Amino Acids, 14. - Diastereoselective Addition of Benzenesulfenyl Chloride to 1-Acryloylproline Esters

(S)-Proline esters (S)-1 react with acryloyl chloride (2) to give 1-acryloylproline esters (S)-3 in good yields.Addition of benzenesulfenyl chloride (6) to (S)-3 at -95 deg C in dichloromethane results in 1-proline esters

Base-Catalysed Epimerization Behavior and Unusual Reactivity of N-Substituted Derivatives of 2,5-Dicarbalkoxypyrrolidine. Preparation of a Novel Mixed Carbamic Carbonic Anhydride by a 4-(Dimethylamino)pyridine-Catalyzed Acylation

The equilibration of cis-trans isomers of 1-substituted 2,5-dicarbalkoxypyrrolidine derivatives (1 = CH2Ph, H, CN, CO2R) results in nearly 1:1 mixtures, contrary to a literature report for 1-benzyl-2,5-dicarbalkoxypyrrolidine.Apparent conversion to the tr