856781-81-2

Usage

Chemical structure

A pyrrole-2-carboxylic acid ester with a benzyl and a methyl substituent

Functional groups

Ester, pyrrole, benzyl, and methyl groups

Application

Commonly used in organic synthesis and medicinal chemistry

Pharmacological properties

Exhibits potential pharmacological properties

Research and development

Being studied for its potential use in the treatment of various diseases

Structural significance

Unique structure and properties make it a valuable tool for research and drug development

Upstream product

• 75857-94-2 (5S)-N-(benzyloxycarbonyl)-5-methoxycarbonyl-2-pyrrolidinone 
• 51-35-4 4R-4-hydroxyproline 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 108645-62-1 N-benzyloxycarbonylproline methyl ester 
• 5211-23-4 N-carbobenzyloxy-L-proline methyl ester 
• 501-53-1 benzyl chloroformate 
• 64187-48-0 methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate 
• 928065-03-6 (2S,4S)-4-iodo-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) ester 

Relevant academic research and scientific papers

Fragment-oriented synthesis: β-elaboration of cyclic amine fragments using enecarbamates as platform intermediates

A strategy for the β-sp3 functionalisation of cyclic amines is described. Regioselective conversion of protected amines to enecarbamates is achieved through electrochemical oxidation; these intermediates can be derivatised by functionalised alkyl halides under photoredox catalysis. The potential of the methods is highlighted by direct growth of a DCP2B-binding fragment. This journal is

Manganese-Catalyzed Desaturation of N-Acyl Amines and Ethers

Enamines and enol ethers are versatile synthons for chemical synthesis. While several methods have been developed to access such molecules, prefunctionalized starting materials are usually required, and direct desaturation methods remain rare. Herein, we report direct desaturation reactions of N-protected cyclic amines and cyclic ethers using a mild I(III) oxidant, PhI(OAc)2, and an electron-deficient manganese pentafluorophenylporphyrin catalyst, Mn(TPFPP)Cl. This system displays high efficiency for α,β-desaturation of various cyclic amines and ethers. Mechanistic probes suggest that the desaturation reaction occurs via an initial α-C-H hydroxylation pathway, which serves to protect the product from overoxidation.

First total synthesis of penmacric acid and its stereoisomer

The total synthesis of penmacric acid and its stereoisomer, epipenmacric acid, is reported for the first time starting from trans-4-hydroxy-l-proline. Et3B-induced diastereoselective radical addition reaction was used to control stereoselectivity at the C3 stereogenic center as a key step.

One-pot synthesis of cyclic enecarbamates from lactam carbamates

A general, practical and efficient one-pot synthesis of cyclic enecarbamates is described. The protocol proceeds via reduction of lactam carbamate with Super-Hydride, followed by in situ dehydration with trifluoroacetic anhydride (TFAA) and diisopropylethylamine (DIPEA).