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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrrolidines Pyrrolidine carboxylic acids and derivatives Pyrrolidine carboxylic acids

Comprehensive Guide to tert-butyl 3-bromo-4-[2-(2-methoxyethoxy)ethoxy]pyrrolidine-1-carboxylate (CAS No. 1693904-75-4)

tert-butyl 3-bromo-4-[2-(2-methoxyethoxy)ethoxy]pyrrolidine-1-carboxylate (CAS No. 1693904-75-4) is a specialized pyrrolidine derivative widely used in pharmaceutical and organic synthesis research. This compound features a unique molecular structure combining a brominated pyrrolidine core with an ether-linked side chain, making it particularly valuable for drug discovery applications. The tert-butyloxycarbonyl (Boc) protecting group enhances its stability during synthetic processes, while the bromo substituent offers excellent reactivity for further functionalization.

Recent interest in pyrrolidine-based compounds has surged due to their importance in developing COVID-19 therapeutics and cancer drugs. Researchers frequently search for "Boc-protected pyrrolidine synthesis" and "ether-functionalized heterocycles," highlighting the relevance of this compound. The presence of both 3-bromo and 4-[2-(2-methoxyethoxy)ethoxy] substituents makes it particularly useful for creating PEG-like modified pharmaceuticals with improved solubility.

The compound's molecular weight of 382.25 g/mol and moderate lipophilicity (predicted LogP ~2.1) make it suitable for central nervous system drug development. Its structural features align with current trends in proteolysis targeting chimera (PROTAC) research, where researchers seek "spacer units for PROTAC design." The flexible ethylene glycol chain may serve as an ideal linker in these emerging therapeutic modalities.

In synthetic applications, tert-butyl 3-bromo-4-[2-(2-methoxyethoxy)ethoxy]pyrrolidine-1-carboxylate serves as a versatile intermediate for Suzuki coupling reactions and nucleophilic substitutions. Pharmaceutical chemists value its ability to introduce both polar solubilizing groups and reactive handles into target molecules. Recent publications highlight its use in creating kinase inhibitors, addressing the growing demand for "new cancer treatment scaffolds" in medicinal chemistry.

The compound's stability under standard laboratory conditions and compatibility with common organic solvents (DCM, THF, DMF) make it practical for diverse research applications. Its spectral characteristics (1H NMR: δ 1.45 (s, 9H), 3.38 (s, 3H), 3.5-3.8 (m, 8H), 4.15 (m, 1H), 4.35 (m, 1H)) provide clear identification markers, important for researchers verifying "pyrrolidine derivative characterization." These properties support its growing use in high-throughput screening libraries.

Market analysis shows increasing demand for functionalized pyrrolidines like this compound, particularly from contract research organizations and academic laboratories working on GPCR-targeted drugs. The combination of Boc protection and bromine functionality offers time-saving advantages in multi-step syntheses, addressing the pharmaceutical industry's need for "efficient synthetic building blocks."

Environmental and safety considerations for tert-butyl 3-bromo-4-[2-(2-methoxyethoxy)ethoxy]pyrrolidine-1-carboxylate follow standard laboratory chemical handling protocols. While not classified as hazardous under GHS criteria, proper personal protective equipment (lab coat, gloves, eye protection) is recommended during handling. The compound's low volatility (predicted vapor pressure: 2.3×10?? mmHg at 25°C) reduces inhalation risks, an important factor for researchers searching "safe heterocyclic compounds."

Future applications may exploit this compound's potential in bioconjugation chemistry and antibody-drug conjugate (ADC) development, particularly for attaching hydrophilic payloads. The triethylene glycol moiety could help address common ADC challenges like aqueous solubility and biodistribution, making it relevant to current "next-generation ADC design" research trends.

For researchers considering tert-butyl 3-bromo-4-[2-(2-methoxyethoxy)ethoxy]pyrrolidine-1-carboxylate (CAS 1693904-75-4) in their work, available literature suggests successful applications in peptide mimetics and small molecule drug candidates. The compound's balanced combination of reactivity and stability positions it as a valuable tool for addressing contemporary challenges in medicinal chemistry and drug discovery programs.

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