56633-75-1

Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-(2-PYRROLIDINYL)ACETIC ACID is used as a starting material for the synthetic preparation of GABA uptake and transport inhibitors. These inhibitors play a significant role in the treatment of various neurological disorders, such as epilepsy, anxiety, and depression, by modulating the activity of the gamma-aminobutyric acid (GABA) neurotransmitter system in the brain.

InChI:InChI=1/C6H11NO2/c8-6(9)4-5-2-1-3-7-5/h5,7H,1-4H2,(H,8,9)/t5-/m0/s1

Upstream product

• 72500-25-5 (S)-benzyl 2-(cyanomethyl)pyrrolidine-1-carboxylate 
• 104553-43-7 (2S,αS)-tert-butyl pyrrolidin-2-yl-acetate 
• 164660-17-7 (3R,4E,αS)-tert-butyl 3-(N-allyl-N-α-methylbenzylamino)-hept-4-enoate 
• 121378-47-0 <(S)-1-Benzyl-2-<(S)-2-(3,3-dimethyl-2-oxobutyl)-pyrrolodino>-2-oxoethyl>-2,2-dimethylpropionat 
• 121378-45-8 1-<(S)-1-((S)-3-Phenyllactoyl)-2-pyrrolidinyl>-3,3-dimethyl-2-butanon 
• 569679-82-9 (3R,αS)-tert-butyl 3-(N-allyl-N-α-methylbenzylamino)-pent-4-enoate 
• 468071-50-3 (2S,αS)-tert-butyl 1-(N-α-methylbenzylamino)-pyrrolidin-2-yl-acetate 
• 468071-45-6 (2R,αS)-tert-butyl 1-(N-α-methylbenzyl)-2,5-dihydro-1H-2-pyrrolyl-acetate 
• 81838-85-9 tert-butyl (2E,4E)-2,4-hexadienoate 
• 16809-92-0 tert-butyl (2E)-penta-2,4-dienoate 
• 121378-49-2 N-<(S)-3-Phenyl-2-(2,2-dimethylpropionyloxy)-propionyl>-(S)-pyrrolidin-2-ylessigsaeure 

Downstream Products

• 175442-65-6 (S)-2-{[2-(2-tert-Butoxycarbonylsulfanyl-ethylsulfanyl)-4-(tert-butyl-dimethyl-silanyloxy)-phenylcarbamoyl]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Nucleophile-dependent regio- and stereoselective ring opening of 1-azoniabicyclo[3.1.0]hexane tosylate

1-[(1R)-(1-Phenylethyl)]-1-azoniabicyclo[3.1.0]hexane tosylate was generated as a stable bicyclic aziridinium salt from the corresponding 2-(3-hydroxypropyl)aziridine upon reaction with p-toluenesulfonyl anhydride. This bicyclic aziridinium ion was then treated with various nucleophiles including halides, azide, acetate, and cyanide in CH3CN to afford either piperidines or pyrrolidines through regio- and stereoselective ring opening, mediated by the characteristics of the applied nucleophile. On the basis of DFT calculations, ring-opening reactions under thermodynamic control yield piperidines, whereas reactions under kinetic control can yield both piperidines and pyrrolidines depending on the activation energies for both pathways. A ring thing: 1-[(1R)-(1-Phenylethyl)]-1-azoniabicyclo[3.1.0]hexane tosylate generated from 2-(3-hydroxypropyl)aziridine with p-toluenesulfonyl anhydride was treated with various nucleophiles including halide, azide, acetate, and cyanide in CH3CN to afford either piperidines or pyrrolidines through regio- and stereoselective ring opening (see scheme).

Asymmetric synthesis of cyclic β-amino acids and cyclic amines via sequential diastereoselective conjugate addition and ring closing metathesis

Diastereoselective conjugate addition of lithium (S)-N-allyl-N-α-methylbenzylamide to a range of α,β-unsaturated esters followed by ring closing metathesis is used to afford efficiently a range of substituted cyclic β-amino esters in high d.e. Alternatively, conjugate addition to α,β-unsaturated Weinreb amides, functional group conversion and ring closing metathesis affords cyclic amines in high d.e. The further application of this methodology to the synthesis of a range of carbocyclic β-amino esters via conjugate addition, enolate alkylation and ring closing metathesis is also described. Application of this methodology affords, after deprotection, (S)-homoproline, (S)-homopipecolic acid, (S)-coniine and (1S,2S)-trans-pentacin.

Ring closing metathesis for the asymmetric synthesis of (S)-homopipecolic acid, (S)-homoproline and (S)-coniine

Diastereoselective conjugate addition of lithium (S)-N-allyl-N-α-methylbenzylamide to α,β-unsaturated esters or Weinreb amides, followed by ring closing metathesis is used to afford the cyclic β-amino acids (S)-homopipecolic acid and (S)-homoproline and the amine (S)-coniine in high ee.

Synthesis of tetradentate bisamino-bisthiol complexes of oxorhenium(V) as structural mimics of steroids

Two tetradentate chelate systems have been synthesized in order to prepare metal complexes with oxorhenium(V) whose structures will mimic that of steroids. The chelate system with amide/amine/thioether/thiol donor sites failed to give a stable complex, bu

Asymetric Electrophilic α-Amidoalkylation 4: Generation and Trapping Reactions of Chiral N-Acylpyrrolidiniumions

The pyrrole derivatives 1, 6, and 10 react in the presence of TiCl4 with the silyl enol ether 3 to form α-substituted pyrrolidine amides stereoselectively. 6 and 10 (after HCl-addition =>11) react even at -78 deg C, the reaction of 10 exceeds that of 6 in yield and stereoselctivity.