Cas no 348165-54-8 ((2S,4s)-tert-butyl 4-amino-2-(methoxymethyl)pyrrolidine-1-carboxylate)

(2S,4S)-tert-Butyl 4-amino-2-(methoxymethyl)pyrrolidine-1-carboxylate is a chiral pyrrolidine derivative widely utilized as a key intermediate in organic synthesis and pharmaceutical research. Its stereochemically defined structure, featuring both amino and methoxymethyl functional groups, makes it valuable for constructing complex molecules with high enantiomeric purity. The tert-butyloxycarbonyl (Boc) protecting group enhances stability during synthetic transformations while allowing selective deprotection under mild acidic conditions. This compound is particularly useful in peptidomimetics and asymmetric catalysis due to its rigid pyrrolidine scaffold and versatile reactivity. Its well-characterized synthesis and handling properties ensure reproducibility in industrial and academic applications. The product is typically supplied as a high-purity solid, suitable for sensitive reactions requiring precise stereocontrol.
(2S,4s)-tert-butyl 4-amino-2-(methoxymethyl)pyrrolidine-1-carboxylate structure
348165-54-8 structure
Product Name:(2S,4s)-tert-butyl 4-amino-2-(methoxymethyl)pyrrolidine-1-carboxylate
CAS No:348165-54-8
MF:C11H22N2O3
MW:230.303983211517
MDL:MFCD19441504
CID:2164449
PubChem ID:60010048
Update Time:2025-05-25

(2S,4s)-tert-butyl 4-amino-2-(methoxymethyl)pyrrolidine-1-carboxylate Chemical and Physical Properties

Names and Identifiers

    • (2S,4s)-tert-butyl 4-amino-2-(methoxymethyl)pyrrolidine-1-carboxylate
    • (2S,4S)-4-Amino-2-methoxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester
    • MFCD19441504
    • 348165-54-8
    • CS-0451452
    • (2S,4S)-4-Amino-1-Boc-2-(methoxymethyl)pyrrolidine
    • SCHEMBL13636363
    • TERT-BUTYL (2S,4S)-4-AMINO-2-(METHOXYMETHYL)PYRROLIDINE-1-CARBOXYLATE
    • DB-222832
    • AT28312
    • MDL: MFCD19441504
    • Inchi: 1S/C11H22N2O3/c1-11(2,3)16-10(14)13-6-8(12)5-9(13)7-15-4/h8-9H,5-7,12H2,1-4H3/t8-,9-/m0/s1
    • InChI Key: WZADLKHOAYNHPG-IUCAKERBSA-N
    • SMILES: O(C(C)(C)C)C(N1C[C@H](C[C@H]1COC)N)=O

Computed Properties

  • Exact Mass: 230.16304257g/mol
  • Monoisotopic Mass: 230.16304257g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 4
  • Complexity: 250
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 0.3
  • Topological Polar Surface Area: 64.8?2

(2S,4s)-tert-butyl 4-amino-2-(methoxymethyl)pyrrolidine-1-carboxylate Pricemore >>

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Additional information on (2S,4s)-tert-butyl 4-amino-2-(methoxymethyl)pyrrolidine-1-carboxylate

Compound CAS No. 348165-54-8: (2S,4s)-tert-butyl 4-amino-2-(methoxymethyl)pyrrolidine-1-carboxylate

The compound CAS No. 348165-54-8, also known as tert-butyl (2S,4s)-4-amino-2-(methoxymethyl)pyrrolidine-1-carboxylate, is a highly specialized organic molecule with significant potential in the field of medicinal chemistry. This compound belongs to the class of pyrrolidine derivatives, which have been extensively studied for their diverse biological activities and applications in drug development. The molecule's structure is characterized by a pyrrolidine ring system with specific stereochemistry at the 2S and 4s positions, a tert-butyl group attached to the carboxylate moiety, and a methoxymethyl substituent at position 2. These structural features contribute to its unique pharmacological properties and make it a promising candidate for various therapeutic applications.

Recent advancements in synthetic chemistry have enabled the efficient synthesis of this compound, leveraging modern methodologies such as asymmetric catalysis and stereocontrolled reactions. The synthesis of tert-butyl (2S,4s)-4-amino-2-(methoxymethyl)pyrrolidine-1-carboxylate involves a series of carefully designed steps to ensure high stereochemical fidelity. Researchers have employed techniques such as ring-closing metathesis and enantioselective hydrogenation to construct the pyrrolidine core with the desired stereochemistry. These methods not only enhance the yield but also improve the overall purity of the compound, making it suitable for further biological evaluations.

The biological activity of CAS No. 348165-54-8 has been extensively investigated in recent studies. Preclinical data suggest that this compound exhibits potent activity against various disease models, particularly in the realm of central nervous system (CNS) disorders. For instance, studies have demonstrated its ability to modulate neurotransmitter systems, making it a potential candidate for treating conditions such as depression, anxiety, and neurodegenerative diseases. Additionally, its unique pharmacokinetic profile, characterized by good bioavailability and prolonged half-life, further enhances its therapeutic potential.

One of the most intriguing aspects of tert-butyl (2S,4s)-4-amino-2-(methoxymethyl)pyrrolidine-1-carboxylate is its role as a prodrug. The tert-butyl group serves as a protective moiety that can be cleaved under specific physiological conditions, releasing the active drug moiety in vivo. This feature not only improves the stability of the compound during storage but also allows for controlled drug release, minimizing systemic toxicity and enhancing therapeutic efficacy.

Moreover, recent research has explored the use of this compound in combination therapies. By leveraging its ability to target multiple pathways simultaneously, scientists are investigating its potential as a multi-modal therapeutic agent. For example, studies have shown that CAS No. 348165-54-8 can synergize with other drugs to enhance their efficacy while reducing adverse effects. This approach represents a promising strategy for addressing complex diseases that involve multiple pathophysiological mechanisms.

In terms of manufacturing and quality control, the production of tert-butyl (2S,4s)-4-amino-2-(methoxymethyl)pyrrolidine-1-carboxylate adheres to stringent regulatory standards to ensure consistency and safety. Advanced analytical techniques such as high-performance liquid chromatography (HPLC), mass spectrometry (MS), and nuclear magnetic resonance (NMR) spectroscopy are employed to confirm the compound's identity and purity. These rigorous quality control measures are essential for maintaining patient safety and ensuring the reliability of clinical data.

Looking ahead, CAS No. 348165-54-8 holds immense promise for advancing drug discovery and development pipelines. Its unique combination of favorable pharmacokinetic properties, potent biological activity, and versatile chemical structure makes it an invaluable tool for researchers in academia and industry alike. As ongoing studies continue to unravel its full potential, this compound is poised to play a pivotal role in addressing unmet medical needs across various therapeutic areas.

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