(S)-2-(Pyrrolidin-3-yl)acetic acid

Base Information

• Chemical Name: (S)-2-(Pyrrolidin-3-yl)acetic acid
• CAS No.: 122442-02-8
• Molecular Formula: C6H11NO2
• Molecular Weight: 129.15704
• DSSTox Substance ID: DTXSID00363602
• Nikkaji Number: J1.020.583B
• ChEMBL ID: CHEMBL349005
• Mol file: 122442-02-8.mol

Synonyms:122442-02-8;(S)-2-(Pyrrolidin-3-yl)acetic acid;2-[(3S)-pyrrolidin-3-yl]acetic acid;(S)-3-Pyrrolidineacetic acid;CHEMBL349005;homo-beta proline;3-Pyrrolidineacetic acid, (3S)-;[S,(+)]-Homo-beta-proline;SCHEMBL24478321;DTXSID00363602;AMY25039;XEA44202;(S)-2-(Pyrrolidin-3-yl)aceticacid;BDBM50013223;AKOS006327684;AS-50635;CS-0052117;EN300-814372;P10779;Pyrrolidin-3-yl-acetic acid ((S)-(+)-Homo beta Proline)

Chemical Property of (S)-2-(Pyrrolidin-3-yl)acetic acid

Chemical Property:

• Melting Point: 178 °C
• Boiling Point: 272.3±13.0 °C(Predicted)
• PKA: 4.43±0.10(Predicted)
• PSA: 49.33000
• Density: 1.104±0.06 g/cm3(Predicted)
• LogP: 0.39940
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: -2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 129.078978594
• Heavy Atom Count: 9
• Complexity: 114

Purity/Quality:

99%, ^*data from raw suppliers

(S)-2-(Pyrrolidin-3-yl)aceticacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNCC1CC(=O)O
• Isomeric SMILES: C1CNC[C@@H]1CC(=O)O
• General Description: (S)-2-(Pyrrolidin-3-yl)acetic acid, also known as (S)-3-pyrrolidineacetic acid, is a non-proteinogenic amino acid with potential applications as an inhibitor of GABA uptake, making it relevant for neurological disorders like Parkinson's disease and epilepsy. Its enantiomerically pure form can be synthesized efficiently via an intramolecular Michael reaction, demonstrating utility in medicinal chemistry for producing bioactive compounds with high stereochemical control.

Technology Process of (S)-2-(Pyrrolidin-3-yl)acetic acid

There total 45 articles about (S)-2-(Pyrrolidin-3-yl)acetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(S)-2-{1-[(benzyloxy)carbonyl]pyrrolidin-3-yl}acetic acid (219560-29-9,264903-86-8) → (S)-(+)-homo-β-proline (122442-02-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; water; for 0.25h;

DOI:10.1016/S0960-894X(98)00532-0

Reference yield: 99.0%

(1S,5S,6S)-di-tert-butyl 2-azabicyclo[3.1.0]hexane-2,6-dicarboxylate → (S)-(+)-homo-β-proline (122442-02-8)

Guidance literature:

(1S,5S,6S)-di-tert-butyl 2-azabicyclo[3.1.0]hexane-2,6-dicarboxylate; With triethylsilane; trifluoroacetic acid; In dichloromethane; at 0 ℃; for 408h; Inert atmosphere; Sealed tube;

With hydrogenchloride; In water; Reagent/catalyst; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.7b01111

Reference yield: 99.0%

(S)-tert-butyl 3-(2-(tert-butoxy)-2-oxoethyl)pyrrolidine-1-carboxylate → (S)-(+)-homo-β-proline (122442-02-8)

Guidance literature:

(S)-tert-butyl 3-(2-(tert-butoxy)-2-oxoethyl)pyrrolidine-1-carboxylate; With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 24h; Inert atmosphere; Sealed tube;

With hydrogenchloride; In water; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.7b01111

upstream raw materials:

(3S)-1-<(R)-1-phenylethyl>pyrrolidine-3-acetic acid

methyl (3S,1'S)-<1-(1'-phenyleth-1'-yl)-pyrrolidin-3-yl> acetate

(S)-2-{1-[(benzyloxy)carbonyl]pyrrolidin-3-yl}acetic acid

(3S)-2-(1-Benzylpyrrolidin-3-yl)acetic acid

Refernces

Diastereomerically pure pyrrolidin-2-ones by intramolecular Michael reaction. Synthesis of both (S)- and (R)-3-pyrrolidineacetic acid

10.1016/0957-4166(95)00423-8

The research focuses on the synthesis of diastereomerically pure pyrrolidin-2-ones and their subsequent conversion into both (S)- and (R)-3-pyrrolidineacetic acids. The purpose of this study is to develop an efficient synthetic route for these non-proteinogenic amino acids, which have potential applications as inhibitors of GABA uptake in neurological disorders such as Parkinson's disease and epilepsy. The researchers achieved this by employing an intramolecular Michael reaction, starting from amides derived from (S)-phenylethylamine. The study successfully demonstrated the synthesis of the target compounds with good yields and high diastereomeric ratios, highlighting the potential of this method for preparing enantiomerically pure 3-pyrrolidineacetic acids.

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