216311-58-9

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-Methyl 1-benzylpyrrolidine-3-carboxylate is used as an intermediate in the pharmaceutical industry for the synthesis of various drugs. Its potential biological activity and unique structure make it a valuable component in the development of new medications.
Used in Agrochemical Synthesis:
In the agrochemical industry, (S)-Methyl 1-benzylpyrrolidine-3-carboxylate is utilized as a key component in the creation of pesticides and other agricultural chemicals. Its versatility and potential biological activity contribute to the effectiveness of these products.
Used in Organic Chemistry:
(S)-Methyl 1-benzylpyrrolidine-3-carboxylate serves as a versatile building block in organic chemistry, allowing for the preparation of a wide range of organic compounds. Its unique structure and functional groups facilitate various chemical reactions and synthesis pathways.
Used in Chiral Synthesis:
As a chiral building block, (S)-Methyl 1-benzylpyrrolidine-3-carboxylate is used in the synthesis of enantiomerically pure chemical compounds. Its stereochemistry is crucial for the development of single-enantiomer drugs, which can have significant implications for the efficacy and safety of pharmaceuticals.
Used in Antihypertensive and Anticonvulsant Research:
(S)-Methyl 1-benzylpyrrolidine-3-carboxylate has been studied for its potential antihypertensive and anticonvulsant properties. It is used as a compound of interest in the research and development of new treatments for hypertension and seizures.

Upstream product

• 67-56-1 methanol 
• 1212293-24-7 (S)-1-Benzyl-pyrrolidine-3-carboxylic acid; hydrochloride 
• 1087209-93-5 C₁₃H₁₇NO₂*ClH 
• 159063-16-8 (S)-1-benzylpyrrolidine-3-carbonitrile 
• 114715-35-4 (R)-3-methanesulfonyloxy-1-(phenylmethyl)-pyrrolidine 
• 159497-65-1 N,N-dibenzylasparaginic acid dibenzyl ester 
• 137428-32-1 (2S)-2-[bis(phenylmethyl)amino]-1,4-butanediol 
• 428518-42-7 (S)-(+)-1-(phenylmethyl)-5-oxo-3-pyrrolidinecarboxylic acid 
• 100-46-9 benzylamine 
• 617-52-7 Dimethyl itakonate 
• 51535-00-3 methyl 1-benzyl-5-oxo-3-pyrrolidinecarboxylate 
• 428518-44-9 methyl (S)-1-(phenylmethyl)-5-oxo-3-pyrrolidinecarboxylate 

Downstream Products

• 216311-60-3 (3S)-pyrrolidine-3-carboxylic acid methyl ester 
• 957785-39-6 (S)-1-benzyl-N-(2,6-dimethylphenyl)-3-pyrrolidinecarboxamide 
• 226088-57-9 (S)-1-methyl-pyrrolidine-3-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Enzymatic resolution of n-substituted-β-prolines

A general and straightforward strategy for enzymatic resolution of N-substituted-β-proline has been successfully designed and developed in our research laboratories. A first affinity screen is followed by ratio enzyme/substrate optimization to source our

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.

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.