tert-Butyl (R)-3-((S)-3-(3-bromophenyl)-1-(tert-butoxy)-1-oxopropan-2-yl)pyrrolidine-1-carboxylate
[CAS# 2565657-65-8]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: tert-Butyl (R)-3-((S)-3-(3-bromophenyl)-1-(tert-butoxy)-1-oxopropan-2-yl)pyrrolidine-1-carboxylate
• Synonyms: 2-methylpropan-2-yl (3R)-3-[(2S)-3-(3-bromophenyl)-1-[(2-methylprop-2-yl)oxy]-1-oxoprop-2-yl]tetrahydropyrrole-1-carboxylate
• Molecular Formula: C₂₂H₃₂BrNO₄
• Molecular Weight: 454.40
• CAS Registry Number: 2565657-65-8
• SMILES: CC(C)(C)OC(=O)[C@@H](CC1=CC(=CC=C1)Br)[C@H]2CCN(C2)C(=O)OC(C)(C)C

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P305+351+338-P302+352

Discovory and Applicatios

tert-Butyl (R)-3-((S)-3-(3-bromophenyl)-1-(tert-butoxy)-1-oxopropan-2-yl)pyrrolidine-1-carboxylate is a specialized chemical compound with significant applications in medicinal chemistry and organic synthesis. The structure of this compound includes a pyrrolidine ring, a key feature in many biologically active molecules, along with a chiral center that imparts stereochemical specificity. The presence of a bromophenyl group and tert-butoxy groups enhances its reactivity and solubility, making it useful for targeted reactions in complex chemical and pharmaceutical research.

This compound was developed as part of ongoing efforts to create more efficient intermediates for synthesizing biologically active molecules. The stereochemical configuration of the pyrrolidine ring and the incorporation of bulky tert-butyl groups suggest a potential for stabilizing specific conformations, which is an important aspect when designing drugs with high selectivity and potency. The (R)- and (S)-specific stereochemistry at different positions in the molecule is essential for tailoring its pharmacological properties and ensuring the desired biological effects.

The discovery and use of tert-Butyl (R)-3-((S)-3-(3-bromophenyl)-1-(tert-butoxy)-1-oxopropan-2-yl)pyrrolidine-1-carboxylate can be traced to the need for more refined synthetic routes for producing chiral intermediates. These intermediates are crucial for building complex molecules, particularly in the development of new therapeutic agents. The combination of a pyrrolidine ring with the functional groups present in this molecule allows it to act as a versatile intermediate for further modification and functionalization.

One of the key applications of this compound lies in the synthesis of pharmaceuticals, particularly those targeting specific receptors or enzymes involved in disease mechanisms. Its ability to participate in selective reactions, particularly in the presence of stereochemical constraints, makes it a valuable tool in the development of drugs with high specificity. For instance, the bromophenyl group and the ester functionality are known to be involved in interactions with various biological targets, enabling the compound to be used as a building block for molecules with enhanced bioactivity.

In addition to drug discovery, this compound also has applications in the synthesis of agrochemicals and other fine chemicals. The versatility provided by the pyrrolidine ring and its functionalization with various groups like the bromophenyl and tert-butoxy moieties expands its potential for creating new materials with desirable properties, such as increased stability or targeted reactivity. The bulky tert-butyl groups, in particular, may provide steric hindrance that can influence the reactivity and selectivity of chemical reactions, making this compound a useful reagent in the synthesis of complex organic molecules.

Moreover, the compound has been studied in the context of asymmetric synthesis, where its chiral centers play an important role. The ability to synthesize compounds with specific chirality is crucial for creating drugs that can interact precisely with biological systems, leading to better therapeutic outcomes with fewer side effects. Researchers have explored its potential in catalytic cycles and other reaction mechanisms that require stereocontrol, further highlighting its value in synthetic organic chemistry.

In conclusion, tert-Butyl (R)-3-((S)-3-(3-bromophenyl)-1-(tert-butoxy)-1-oxopropan-2-yl)pyrrolidine-1-carboxylate is a highly functionalized chiral compound with diverse applications in medicinal chemistry, organic synthesis, and agrochemical production. Its stereochemical specificity and functional group reactivity make it a valuable intermediate in the development of new therapeutic agents and complex organic molecules.