216311-60-3

Basic information

• Product Name: 3-Pyrrolidinecarboxylic acid, methyl ester, (3S)- (9CI)
• Synonyms: 3-Pyrrolidinecarboxylic acid, methyl ester, (3S)- (9CI);(S)-methyl pyrrolidine-3-carboxylate;(3S)-3-Pyrrolidinecarboxylic acid Methyl ester;3-Pyrrolidinecarboxylic acid, Methyl ester, (3S)-;Methyl (3S)-pyrrolidine-3-carboxylate
• CAS NO: 216311-60-3
• Molecular Formula: C₆H₁₁NO₂
• Molecular Weight: 129.15704
• Product Categories: ACIDHALIDE
• Mol File: 216311-60-3.mol

Chemical Properties

• Boiling Point: 170℃
• Flash Point: 57℃
• Appearance: /
• Density: 1.055
• Storage Temp.: Keep in dark place,Sealed in dry,Store in freezer, under -20°C
• PKA: 9.42±0.10(Predicted)
• CAS DataBase Reference: 3-Pyrrolidinecarboxylic acid, methyl ester, (3S)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pyrrolidinecarboxylic acid, methyl ester, (3S)- (9CI)(216311-60-3)
• EPA Substance Registry System: 3-Pyrrolidinecarboxylic acid, methyl ester, (3S)- (9CI)(216311-60-3)

Safety Data

• Hazardous Substances Data: 216311-60-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-Pyrrolidinecarboxylic acid, methyl ester, (3S)(9CI) is used as a chiral building block in organic synthesis for the production of various compounds. Its unique (3S)configuration allows for the creation of enantiomerically pure products, which is crucial for the development of pharmaceuticals and agrochemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Pyrrolidinecarboxylic acid, methyl ester, (3S)(9CI) is used as a key intermediate in the synthesis of drugs with specific biological activities. Its chiral nature ensures that the final drug product has the desired therapeutic effects while minimizing potential side effects.
Used in Agrochemical Industry:
3-Pyrrolidinecarboxylic acid, methyl ester, (3S)(9CI) is also utilized in the agrochemical industry for the synthesis of chiral pesticides and other agrochemicals. The (3S)configuration of this compound allows for the development of more effective and targeted agrochemicals with reduced environmental impact.

Upstream product

• 1212293-24-7 (S)-1-Benzyl-pyrrolidine-3-carboxylic acid; hydrochloride 
• 159063-16-8 (S)-1-benzylpyrrolidine-3-carbonitrile 
• 428518-44-9 methyl (S)-1-(phenylmethyl)-5-oxo-3-pyrrolidinecarboxylate 
• 428518-42-7 (S)-(+)-1-(phenylmethyl)-5-oxo-3-pyrrolidinecarboxylic acid 
• 617-52-7 Dimethyl itakonate 
• 51535-00-3 methyl 1-benzyl-5-oxo-3-pyrrolidinecarboxylate 
• 216311-58-9 methyl (S)-(+)-1-(phenylmethyl)-3-pyrrolidinecarboxylate 

Downstream Products

• 1611445-30-7 (S)-1-(4’-(4-(trifluoromethyl)cyclohexyloxy)biphenylcarbonyl)pyrrolidine-3-carboxylic acid 
• 1446492-42-7 C₃₀H₃₆ClFN₂O₅ 
• 1446492-35-8 C₂₈H₃₂ClFN₂O₅ 
• 1446492-15-4 C₂₈H₃₂ClFN₂O₆ 
• 1446492-16-5 C₂₇H₃₀ClFN₂O₆ 
• 226088-57-9 (S)-1-methyl-pyrrolidine-3-carboxylic acid methyl ester 

Relevant articles and documents

A chemoenzymatic approach to the synthesis of enantiomerically pure aza analogues of paraconic acid methyl ester and both enantiomers of methyl β-proline

Enantiopure methyl esters of 1-alkyl-5-oxo-3-pyrrolidinecarboxylic acids were obtained by enzymatic resolution of the corresponding chiral racemic mixtures. A particularly favourable interaction, also supported by molecular mechanics calculations, was observed between the 1-benzyl derivative and α-chymotrypsin, for which the enantiomeric ratio, E, exceeded 200. The absolute configurations of the lactams were determined by means of CD spectroscopy. From the resulting enantiomerically pure (99% e.e.) (S)-(+)-1-benzyl-3-pyrrolidinecarboxylic acid and methyl (R)-(-)-1-benzyl-3-pyrrolidinecarboxylate, the methyl esters of (+) and (-)-β-proline were synthesised in 99% e.e. and 18 and 22% overall yield, respectively.

Ex-chiral pool synthesis and pharmacological aspects of 3- pyrrolidinylisoxazoles

Employing the dopamine autoreceptor agonist (-)-3-PPP (3) as well as the cholinergic receptor ligands 4 and 5 as lead compounds the 3- pyrrolidinylisoxazoles 2a,b as well as its optical antipodes ent-2a,b were synthesized from (R)-aspartic acid (6) and (S)-aspartic acid (ent-6), respectively. Pharmacological properties of the target compounds were evaluated employing dopamine D2 receptor binding studies and functional experiments on muscarinic M2 receptors.

A practical ex-chiral-pool synthesis of β-proline and homo-β-proline

Starting from aspartic acid an efficient synthesis of enantiomerically pure β-proline and homo-β-proline is described. The key step of the synthesis includes formation of the 1,4-biselectrophile 6, followed by rearrangement via the aziridinium intermediate 7 and ring closure to give the pyrrolidinium salt 9a which can serve as a common precursor for both target compounds.