194154-91-1

Basic information

• Product Name: 2-Pyrrolidineacetic acid, 1-[(1,1-dimethylethoxy)carbonyl]-
• Synonyms: 2-Pyrrolidineacetic acid, 1-[(1,1-dimethylethoxy)carbonyl]-;2-(1-Boc-pyrrolidin-2-yl)acetic acid;[1-(tert-Butoxycarbonyl)pyrrolidin-2-yl]acetic acid;1-(tert-Butoxycarbonyl)-2-(carboxymethyl)pyrrolidine, 2-(Carboxymethyl)pyrrolidine, N-BOC protected;1-BOC-2-PYRROLIDINEACETIC ACID(WX611185);N-Boc-Pyrrolidin-2-yl-acetic acid
• CAS NO: 194154-91-1
• Molecular Formula: C₁₁H₁₉NO₄
• Molecular Weight: 229
• Mol File: 194154-91-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 357.4°C at 760 mmHg
• Flash Point: 169.9°C
• Appearance: /
• Density: 1.151g/cm³
• Vapor Pressure: 4.5E-06mmHg at 25°C
• Refractive Index: 1.491
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-Pyrrolidineacetic acid, 1-[(1,1-dimethylethoxy)carbonyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyrrolidineacetic acid, 1-[(1,1-dimethylethoxy)carbonyl]-(194154-91-1)
• EPA Substance Registry System: 2-Pyrrolidineacetic acid, 1-[(1,1-dimethylethoxy)carbonyl]-(194154-91-1)

Safety Data

• Hazardous Substances Data: 194154-91-1(Hazardous Substances Data)

Usage

General Description

2-Pyrrolidineacetic acid, 1-[(1,1-dimethylethoxy)carbonyl]- is an organic compound with a chemical formula C11H19NO4. It is a derivative of pyrrolidineacetic acid and is commonly used as a building block in the synthesis of various pharmaceuticals and biologically active compounds. 2-Pyrrolidineacetic acid, 1-[(1,1-dimethylethoxy)carbonyl]- is a prodrug, which means that it is converted into its active form in the body after administration. It is often used as a protecting group for amines in organic chemistry synthesis due to its stability and ease of removal. Additionally, it has potential as an anti-inflammatory and anticonvulsant agent, although further research is needed to fully understand its pharmacological properties.

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

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

Downstream Products

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

Relevant articles and documents

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.

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.