132482-05-4

Basic information

• Product Name: (R)-METHYL 2-(PYRROLIDIN-2-YL)ACETATE
• Synonyms: (R)-METHYL 2-(PYRROLIDIN-2-YL)ACETATE;(R)-tert-Butyl 2-(2-Methoxy-2-oxoethyl)pyrrolidine-1-carboxylate
• CAS NO: 132482-05-4
• Molecular Formula: C₁₂H₂₁NO₄
• Molecular Weight: 143.185
• Mol File: 132482-05-4.mol

Chemical Properties

• Boiling Point: 190.215°C at 760 mmHg
• Flash Point: 68.84°C
• Appearance: /
• Density: 1.006g/cm³
• Vapor Pressure: 0.548mmHg at 25°C
• Refractive Index: 1.44
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (R)-METHYL 2-(PYRROLIDIN-2-YL)ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-METHYL 2-(PYRROLIDIN-2-YL)ACETATE(132482-05-4)
• EPA Substance Registry System: (R)-METHYL 2-(PYRROLIDIN-2-YL)ACETATE(132482-05-4)

Safety Data

• Hazardous Substances Data: 132482-05-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-METHYL 2-(PYRROLIDIN-2-YL)ACETATE is used as a chiral building block for the development of new drug candidates. Its unique structure allows for the creation of enantiomerically pure compounds, which is crucial in pharmaceuticals where the stereochemistry of a molecule can significantly impact its efficacy and safety.
Used in Organic Synthesis:
In the field of organic synthesis, (R)-METHYL 2-(PYRROLIDIN-2-YL)ACETATE serves as a valuable precursor for the synthesis of natural products and complex organic molecules. Its pyrrolidine ring and ester functionality provide a versatile platform for further chemical modifications and reactions.
Used in Drug Development:
(R)-METHYL 2-(PYRROLIDIN-2-YL)ACETATE is also being investigated for its potential use in drug development. Its presence in various biologically active molecules suggests that it may possess药理活性, which could be harnessed for the treatment of specific diseases or conditions. However, further research is necessary to fully understand its potential applications and effects.

InChI:InChI=1/C7H13NO2/c1-10-7(9)5-6-3-2-4-8-6/h6,8H,2-5H2,1H3/t6-/m1/s1

Upstream product

• 186581-53-3 diazomethane 
• 34619-03-9 tert-butyldicarbonate 
• 147-85-3 L-proline 
• 67-56-1 methanol 
• 101130-03-4 tert-butyl (S)-2-(diazoacetyl)pyrrolidine-1-carboxylate 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 84890-94-8 (S)-2-Isobutoxycarbonyloxycarbonyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 223118-68-1 tert-butyl (E)-2-(2-methoxy-2-oxoethylidene)pyrrolidine-1-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 86971-65-5 pyrrolidin-2-ylidene-acetic acid methyl ester 
• 141874-26-2 N-Boc-(S)-proline chloride 
• 259868-83-2 (S)-pyrrolidin-2-ylacetic acid methyl ester hydrochloride 
• 56502-01-3 (2S)-1-tert-butoxycarbonyl-2-carboxymethylpyrrolidine 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 1338968-17-4 C₂₉H₄₁NO₃ 
• 1178977-16-6 (S)-1,1-bis(4-propylphenyl)-2-(pyrrolidin-2-yl)ethanol 
• 1338968-19-6 C₃₃H₄₉NO₃ 
• 1178977-17-7 (S)-1,1-bis(4-pentylphenyl)-2-(pyrrolidin-2-yl)ethanol 
• 1338968-20-9 C₂₇H₂₅F₁₂NO₃ 
• 1178977-14-4 (S)-1,1-bis(3,5-bis(trifluoromethyl)phenyl)-2-(pyrrolidin-2-yl)ethanol 
• 1178977-11-1 (S)-1,1-diphenyl-2-(pyrrolidin-2-yl)ethanol 
• 1338968-21-0 C₁₉H₂₁NO₂ 
• 1338968-22-1 C₂₁H₂₅NO₂ 
• 1338968-24-3 C₂₅H₃₃NO₃ 
• 1338968-04-9 C₂₃H₃₁NO 
• 1178977-28-0 C₂₀H₂₅NO 
• 1338968-12-9 C₂₃H₂₉NO₃ 
• 1338968-14-1 C₂₅H₃₃NO₃ 

Relevant articles and documents

LIGAND EFFECTS IN ENANTIOFACE DIFFERENTIATING 1,4 ADDITION TO 1,3 DIPHENYL-2 PROPEN-1 ONE

The extent of enantiomeric excess in the β-methylation of chalcone by chiral cuprates is shown to depend strongly on small structural modifications of the ligands, all of which are derived from the basic carbon framework of L-prolinol.Enantiomeric excesses up to 88percent have been realised.

Asymmetric synthesis of homoproline derivatives via Rh(I)-catalyzed hydrogenation using chiral bisphosphines as ligands

It has been demonstrated for the first time that Rh(I)-catalyzed asymmetric hydrogenation of cyclic β-enamino acid derivatives 1 using chiral bisphosphines could be a highly efficient synthetic method for optically active homoproline derivatives. The enantioselectivity and conversion yield were largely dependent upon the chiral ligand. Using the Me-BDPMI forming a seven-membered metal chelate, the N-acetylated β-enamino acid methyl ester 1a was hydrogenated to give optically active homoproline derivative 2a with 100% conversion and 96% ee.

Diastereoselective synthesis of (-)-1-methyl-(3S,4R)-3,4-bis((2S)-N- (tert-butyloxycarbonyl)pyrrolidin-2-yl)-2-pyrrolidinone by an asymmetric Michael reaction

Beginning with enantiomerically pure L-proline, (-)-1-methyl-(3S,4R)- 3,4-bis((2S)-N-(tert-butyloxycarbonyl)pyrrolidin-2-yl)-2-pyrrolidinone was prepared in diastereomerically pure form. Taking advantage of the chiral induction of the L-proline derivatives, the intermolecular Michael reaction, used to build the pyrrolidinone ring, was carried out stereoselectively.

Tetrahydropyrido [3, 4-d] pyrimidine derivative and medical application thereof

The invention relates to a compound as shown in a general formula (I) or a stereoisomer, a deuterated compound, a solvate, a prodrug, a metabolite, a pharmaceutically acceptable salt or eutectic crystal thereof, an intermediate and a preparation method thereof, and application of the compound in preparation of drugs for treating diseases related to KRas-G12C activity or expression quantity.

Iminium ion-enamine cascade cyclizations: Facile access to structurally diverse azacyclic compounds and natural products

A one-pot, mild, two-component iminium ion-enamine cascade reaction to construct structurally diverse azacyclic frameworks from l-proline and l-pipecolic acid, and its application to indolizidine and quinolizidine alkaloids and azasteroids, is reported.

Kinetic deconjugation: A gateway to the synthesis of Xxx-Gly (E)-alkene dipeptide isosteres

A new method for the preparation of Xxx-Gly (E)-alkene dipeptide isosteres (EADIs), using LDA deprotonation followed by 1 N HCl quench, was explored. The method, named kinetic deconjugation, enabled the synthesis of Tyr-Gly, Gly-Gly, Ser-Gly, Pro-Gly, and

A systematic study of chiral homoprolinols and their derivatives in the catalysis of enantioselective addition of diethylzinc to aldehydes

Homoprolinol analogs, a class of optically active γ-amino alcohols, were examined systematically in the enantioselective addition reactions of diethylzinc to aldehydes. By comparison of the results catalyzed by these γ-amino alcohols with those by the β-amino alcohols based on pyrrolidine architecture reported in the literature references, we have observed that the γ-amino alcohols are superior to the corresponding β-amino alcohols when the nitrogen and the oxygen are unsubstituted. Among the homoprolinols we tested, 2b gave the best results (45-88% yields, 44-81% ee) in the addition reactions. To the best of our knowledge, 2b has been noticed as one of the most efficient γ-amino alcohol catalysts based on pyrrolidine framework.

Efficient Arndt-Eistert synthesis of selective 5-HT7 receptor antagonist SB-269970

This contribution describes a novel Arndt-Eistert approach for the efficient synthesis of the potent and selective 5-HT7-antagonist, (R)-3-(2-(2-(4-methylpiperidin-1-yl)-ethyl)pyrrolidine-1-sulfonyl)phenol (SB-269970), from D-proline. The synthesis was ca

Asymmetric synthesis of Sedum alkaloids via lithium amide conjugate addition

Conjugate addition of lithium (R)-N-allyl-N-(α-methylbenzyl)amide or lithium (R)-N-but-3-enyl-N-(α-methylbenzyl)amide to an alkyl hexa-2,4-dienoate or alkyl hepta-2,6-dienoate, followed by ring-closing metathesis of the olefin functionalities within the resultant β-amino ester, generates a range of diastereoisomerically pure azacycles in good yield. These homochiral templates are readily transformed to a range of piperidine alkaloids of the Sedum family, and the corresponding five-, seven- and eight-membered ring homologues.

N-acylpyrrolidin-2-ylalkylbenzamidine derivatives as inhibitors of factor Xa

This invention is directed to N-acylpyrrolidin-2-ylalkylbenzamidine derivatives which useful for inhibiting the activity of Factor Xa, by contacting said derivatives with a composition containing Factor Xa. The present invention is also directed to compositions containing said derivatives, methods for their preparation, their use, such as in inhibiting the formation of thrombin or for treating a patient suffering from, or subject to, a disease state associated with a physiologically detrimental excess amount of thrombin.