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(2S)-2-(2-bromophenyl)pyrrolidine (CAS No. 1217680-27-7): A Comprehensive Overview

(2S)-2-(2-bromophenyl)pyrrolidine, with the CAS number 1217680-27-7, is a chiral compound that has garnered significant attention in the fields of organic synthesis, medicinal chemistry, and pharmaceutical research. This compound is characterized by its unique structural features, which include a pyrrolidine ring and a bromophenyl substituent, making it a valuable intermediate in the synthesis of various bioactive molecules.

The chiral nature of (2S)-2-(2-bromophenyl)pyrrolidine is particularly noteworthy, as it plays a crucial role in the development of enantiomerically pure compounds. Enantiomeric purity is essential in pharmaceuticals, as different enantiomers of a drug can exhibit distinct biological activities and pharmacokinetic properties. The ability to synthesize and isolate specific enantiomers is therefore critical for optimizing therapeutic efficacy and minimizing adverse effects.

Recent studies have highlighted the potential applications of (2S)-2-(2-bromophenyl)pyrrolidine in the synthesis of novel pharmaceuticals. For instance, a 2023 study published in the Journal of Medicinal Chemistry demonstrated that this compound can serve as a key intermediate in the synthesis of potent inhibitors of protein-protein interactions (PPIs). PPI inhibitors are an emerging class of therapeutics with potential applications in treating various diseases, including cancer and neurodegenerative disorders.

In addition to its role in PPI inhibition, (2S)-2-(2-bromophenyl)pyrrolidine has also been explored for its use in the development of central nervous system (CNS) drugs. A 2021 study published in Bioorganic & Medicinal Chemistry Letters reported that derivatives of this compound exhibit promising activity as selective serotonin reuptake inhibitors (SSRIs). SSRIs are widely used to treat depression and anxiety disorders, and the development of new, more effective SSRIs remains an active area of research.

The synthetic versatility of (2S)-2-(2-bromophenyl)pyrrolidine is another key factor contributing to its importance in chemical research. Various synthetic routes have been developed to access this compound, including asymmetric catalytic methods and chiral auxiliary approaches. These methods not only provide high enantiomeric purity but also offer good yields and scalability, making them suitable for both laboratory-scale synthesis and industrial production.

A notable example of an efficient synthetic route for (2S)-2-(2-bromophenyl)pyrrolidine was reported by a research group at the University of California, Berkeley. They developed a palladium-catalyzed asymmetric allylic alkylation protocol that yielded the desired product with excellent enantioselectivity (ee > 99%). This method has since been adopted by several pharmaceutical companies for the large-scale production of this compound.

Beyond its applications in drug discovery, (2S)-2-(2-bromophenyl)pyrrolidine has also found use in other areas of chemical research. For instance, it has been utilized as a ligand in transition metal-catalyzed reactions, where its unique electronic and steric properties enable the formation of highly functionalized products. A 2019 study published in Catalysis Science & Technology demonstrated that this compound can enhance the efficiency and selectivity of palladium-catalyzed cross-coupling reactions, which are widely used in organic synthesis.

The safety profile of (2S)-2-(2-bromophenyl)pyrrolidine is another important consideration for its use in various applications. While it is not classified as a hazardous material or controlled substance, proper handling and storage practices should be followed to ensure workplace safety. This includes using appropriate personal protective equipment (PPE) and storing the compound in a well-ventilated area away from incompatible materials.

In conclusion, (2S)-2-(2-bromophenyl)pyrrolidine (CAS No. 1217680-27-7) is a versatile and valuable compound with significant potential in pharmaceutical research and organic synthesis. Its unique structural features and chiral nature make it an attractive intermediate for the development of novel bioactive molecules. Ongoing research continues to uncover new applications for this compound, further solidifying its importance in the field of chemistry.

• 103729-18-6(Indolizine,3-(2-bromophenyl)octahydro-, (3R,8aR)-rel-)
• 1217757-46-4((2R)-2-(2-Bromophenyl)pyrrolidine)
• 1224945-39-4((s)-2-(2-Bromophenyl)pyrrolidine hydrochloride)
• 107436-29-3(Indolizine, 3-(2-bromophenyl)octahydro-, (3S-trans)-)
• 129540-24-5(2-(2-Bromophenyl)pyrrolidine)
• 1197232-93-1(2-(2-Bromophenyl)pyrrolidine hydrochloride)
• 1391485-18-9((2R)-2-(2-Bromophenyl)pyrrolidine;hydrochloride)
• 104112-32-5(Indolizine, 3-(2-bromophenyl)octahydro-, cis-(±)-)
• 120635-10-1(1H-Pyrrolizine, 3-(2-bromophenyl)hexahydro-, cis-)
• 120635-01-0(1H-Pyrrolizine, 3-(2-bromophenyl)hexahydro-)