194154-91-1

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Pyrrolidineacetic acid, 1-[(1,1-dimethylethoxy)carbonyl]is used as a building block for the synthesis of various pharmaceuticals and biologically active compounds. Its versatile structure allows for the development of new drugs with potential therapeutic applications.
Used as a Protecting Group in Organic Chemistry:
In organic chemistry synthesis, 2-Pyrrolidineacetic acid, 1-[(1,1-dimethylethoxy)carbonyl]is used as a protecting group for amines. Its stability and ease of removal make it a valuable tool in the synthesis of complex organic molecules.
Used in Anti-inflammatory Applications:
2-Pyrrolidineacetic acid, 1-[(1,1-dimethylethoxy)carbonyl]has potential as an anti-inflammatory agent. It may be used to develop treatments for various inflammatory conditions, although further research is needed to confirm its efficacy and safety.
Used in Anticonvulsant Applications:
2-Pyrrolidineacetic acid, 1-[(1,1-dimethylethoxy)carbonyl]also shows promise as an anticonvulsant agent. It could be utilized in the development of medications for the treatment of epilepsy and other seizure disorders, pending further investigation into its pharmacological properties and clinical effectiveness.
Used in Research and Development:
2-Pyrrolidineacetic acid, 1-[(1,1-dimethylethoxy)carbonyl]is used in research and development for the discovery of new drug candidates and the advancement of pharmaceutical technologies. Its unique properties and potential applications make it a valuable compound for scientific exploration.

InChI:InChI=1/C11H19NO4/c1-11(2,3)16-10(15)12-6-4-5-8(12)7-9(13)14/h8H,4-7H2,1-3H3,(H,13,14)

Upstream product

• 146337-04-4 N-[(1,1-dimethylethoxy)carbonyl]-2-(2-propen-1-yl)pyrrolidine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 5027-77-0 homoproline ethyl ester acetate 
• 118758-56-8 tert-butyl 2-(2-ethoxy-2-oxoethyl)pyrrolidine-1-carboxylate 

Downstream Products

• 915233-35-1 2-[3-(4-fluoro-phenyl)-[1,2,4]oxadiazol-5-ylmethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 170491-62-0 2-(2-oxoethyl)pyrrolidine-1-carboxylic acid tert-butyl ester 
• 2407-99-0 hexahydroindolizin-7(1H)-one 
• 958026-65-8 2-(2-bromo-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 220312-34-5 2-(2-hydroxyethyl)pyrrolidine-1-carboxylic acid tert-butyl ester 
• 915233-36-2 3-(4-fluoro-phenyl)-5-pyrrolidin-2-ylmethyl-[1,2,4]oxadiazole hydrochloride 
• 813433-68-0 2-methoxycarbonylmethylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 905717-08-0 tert-butyl 2-(2-oxo-4-phenylbut-3-ynyl)pyrrolidine-1-carboxylate 

Relevant academic research and scientific papers

Process for producing enantiopure beta-amino acid derivatives, and enantiopure beta-amino acid derivatives

Process for producing enantiopure β-amino acid derivatives corresponding to general formula (I) R1-NZ-CHR2—CH2—COOR3 (I) in which R1 and R2 independently denote organic residues optionally forming a cyclic substituent, R3 denotes H or an organic residue, and Z represents H or an amino function-protecting group, comprising a step in which a mixture of enantiomers of a compound corresponding to general formula (II) R1-NZ-CHR2—CH2—COOR4 (II) in which R1, R2 and Z are as defined for formula (I), and R4 is an organic residue, is subjected to hydrolysis in the presence of a lipase.

Enzymatic resolution of cyclic N-Boc protected β-aminoacids

Methyl and ethyl esters of N-Boc homoproline, homopipecolic acid and 3-carboxymethyl-morpholine were kinetically resolved by hydrolysis catalysed by Burkholderia cepacia lipase to give the corresponding acids and residual esters in enantiomeric excesses better than 99% (E > 100).

Homoproline homologation by enolate Claisen rearrangement or direct allylation: Syntheses of (-)-trachelanthamidine, (-)-isoretronecanol and (±)-turneforcidine

The pyrrolizidine precursors 13 and 14 are obtained both by enolate Clalsen rearrangement of the homoproline allyl ester 12 and by direct allylation of N-protected homoproline ethyl ester 15. In both cases, the reactions show poor levels of stereoselectivity. Reduction gives the corresponding alcohols 20a and 21 a which are separated and subsequently elaborated to (-)-trachelanthamidine 24 and (-)-isoretronecanol 25 respectively via reductive alkene cleavage, mesylation and spontaneous cyclisation following N-deprotection. The chiral integrity of the original proline-derived asymmetric centre is preserved throughout. A similar enolate allylation gives, with high stereoselectivity, the homologue 34 of the Geissman-Waiss lactone 32, which is similarly transformed into (±)-turneforcidine 31.