80546-89-0

Basic information

• Product Name: 3-Pyrrolidinecarboxylicacid,4-amino-,cis-(9CI)
• Synonyms: 3-Pyrrolidinecarboxylicacid,4-amino-,cis-(9CI)
• CAS NO: 80546-89-0
• Molecular Formula: C5H10N2O2
• Molecular Weight: 130.15
• Product Categories: PYRROLIDINE;AMINOACID
• Mol File: 80546-89-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 288.6±40.0 °C(Predicted)
• Appearance: /
• Density: 1.244±0.06 g/cm3(Predicted)
• PKA: 2.92±0.20(Predicted)
• CAS DataBase Reference: 3-Pyrrolidinecarboxylicacid,4-amino-,cis-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pyrrolidinecarboxylicacid,4-amino-,cis-(9CI)(80546-89-0)
• EPA Substance Registry System: 3-Pyrrolidinecarboxylicacid,4-amino-,cis-(9CI)(80546-89-0)

Safety Data

• Hazardous Substances Data: 80546-89-0(Hazardous Substances Data)

Upstream product

• 79522-72-8 (E/Z)-(2-propenylamino)acetaldehyde O-methyloxime 
• 474759-01-8 1,1-dimethylethyl (E/Z)-N-[2-(methoxyimino)ethyl]-N-(2-propenyl)carbamate 
• 569682-65-1 (+)-cis-(4S,3R)-4-benzylaminopyrrolidine-1,3-dicarboxylic acid-1-benzyl ester 
• 797038-63-2 tert-butyl (3R,4R)-N-tert-butyloxycarbonyl-4-aminopyrrolidine-3-carboxylate 
• 698358-08-6 tert-butyl 1-(phenylmethyl)-2,5-dihydropyrrole-3-carboxylate 
• 569682-63-9 (-)-N-[2-(1,3-dioxo-1λ⁴,3λ⁴-dithian-2-ylidene)ethyl]-N-(2,2-dimethoxyethyl)carbamic acid benzyl ester 
• 569682-64-0 (+)-[1'R,3'R]-1-benzyl-1',3'-dioxospiro[1',3'-dithiane-2',3-pyrrolo[3,4-c]isoxazole]-5-carboxylic acid benzyl ester 

Relevant articles and documents

Asymmetric synthesis of the cis- And trans-stereoisomers of 4-aminopyrrolidine-3-carboxylic acid and 4-aminotetrahydrofuran-3-carboxylic acid

The diastereoselective conjugate addition of lithium (S)-N-benzyl-N- α-methylbenzylamide has been successfully applied to the first asymmetric syntheses of cis-(3S,4R)- and fraBs-(3R,4R)-4-arninotetrahydrofuran-3-carboxylic acids (26% and 25% overall yield respectively, >98% d.e. and >97% e.e. in each case). Furthermore, the most efficient asymmetric synthesis to date of cis-(3R,4R)- and trans-(3R,4S)-4-aminopyrrolidine carboxylic acids is delineated: for cis-(3R,4R), four steps, >98% d.e., 52% overall yield; for trans-(3R,4S), five steps, >98% d.e., 50% overall yield.

Radical cyclization in heterocycle synthesis. Part 13: Sulfanyl radical addition-cyclization of oxime ethers and hydrazones connected with alkenes for synthesis of cyclic β-amino acids

A combination of sulfanyl radical addition-cyclization of the oxime ethers and hydrazones connected with alkenes and subsequent conversion of a phenylsulfanylmethyl group to a carboxyl group provides a novel method for the construction of the cyclic β-amino acids. Upon treatment with thiophenol in the presence of AIBN, the oxime ethers and hydrazones smoothly underwent sulfanyl radical addition-cyclization to give the 2-(phenylsulfanylmethyl)cycloalkylamine. This method was successfully applied to the practical synthesis of 2-aminocyclopentanecarboxylic acid and 4-amino-3-pyrrolidinecarboxylic acid.