Cas no 1027775-28-5 (tert-butyl (2R)-2-methyl-4-oxopyrrolidine-1-carboxylate)

Technical Introduction: tert-Butyl (2R)-2-methyl-4-oxopyrrolidine-1-carboxylate is a chiral pyrrolidinone derivative featuring a tert-butoxycarbonyl (Boc) protecting group, which enhances stability and facilitates selective deprotection in synthetic applications. The stereogenic center at the 2-position (R-configuration) makes it valuable for asymmetric synthesis, particularly in pharmaceutical intermediates and peptidomimetics. Its oxopyrrolidine scaffold is versatile for constructing heterocyclic frameworks, while the Boc group ensures compatibility with a range of reaction conditions. This compound is commonly employed in medicinal chemistry for its predictable reactivity and utility in multi-step syntheses. High purity grades are available to meet rigorous research and industrial standards.
tert-butyl (2R)-2-methyl-4-oxopyrrolidine-1-carboxylate structure
1027775-28-5 structure
Product Name:tert-butyl (2R)-2-methyl-4-oxopyrrolidine-1-carboxylate
CAS No:1027775-28-5
MF:C10H17NO3
MW:199.246883153915
MDL:MFCD22665783
CID:2155025
PubChem ID:58432539
Update Time:2025-06-08

tert-butyl (2R)-2-methyl-4-oxopyrrolidine-1-carboxylate Chemical and Physical Properties

Names and Identifiers

    • 1-Pyrrolidinecarboxylic acid, 2-methyl-4-oxo-, 1,1-dimethylethyl ester, (2r)-
    • 2-Methyl-2-propanyl (2R)-2-methyl-4-oxo-1-pyrrolidinecarboxylate
    • (R)-tert-butyl 2-Methyl-4-oxopyrrolidine-1-carboxylate
    • N-t-BOC-(R)-2-Methyl-4-Pyrrolidinone
    • ABBMDHUKQONVIE-SSDOTTSWSA-N
    • FCH3535468
    • OR316080
    • N-t-BOC-(R)-2-methyl-4-pyrrolidinone, AldrichCPR
    • tert-butyl (R)-2-methyl-4-oxopyrrolidine-1-carboxylate
    • 1-Pyrrolidinecarboxylic acid,2-methyl-4-oxo-,1,1-dimethylethyl ester,(2R)-
    • tert-butyl (2R)-2-methyl-4-oxopyrrolidine-1-carboxylate
    • (2R)-2-Methyl-4-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
    • D79074
    • MFCD22665783
    • SCHEMBL4881771
    • AKOS037647360
    • EN300-7180391
    • AS-73426
    • DB-419121
    • 1027775-28-5
    • (2R)-1-Boc-2-methyl-4-oxopyrrolidine
    • MDL: MFCD22665783
    • Inchi: 1S/C10H17NO3/c1-7-5-8(12)6-11(7)9(13)14-10(2,3)4/h7H,5-6H2,1-4H3/t7-/m1/s1
    • InChI Key: ABBMDHUKQONVIE-SSDOTTSWSA-N
    • SMILES: O(C(N1CC(C[C@H]1C)=O)=O)C(C)(C)C

Computed Properties

  • Exact Mass: 199.12084340g/mol
  • Monoisotopic Mass: 199.12084340g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 2
  • Complexity: 255
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 46.6
  • XLogP3: 1.1

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Additional information on tert-butyl (2R)-2-methyl-4-oxopyrrolidine-1-carboxylate

Introduction to tert-butyl (2R)-2-methyl-4-oxopyrrolidine-1-carboxylate (CAS No. 1027775-28-5)

tert-butyl (2R)-2-methyl-4-oxopyrrolidine-1-carboxylate (CAS No. 1027775-28-5) is a versatile compound with significant applications in the fields of organic synthesis, medicinal chemistry, and pharmaceutical research. This compound is a chiral derivative of pyrrolidine, characterized by its unique structural features and chemical properties. The presence of the tert-butyl group and the chiral center at the 2-position make it an important building block in the synthesis of various bioactive molecules and drug candidates.

The tert-butyl (2R)-2-methyl-4-oxopyrrolidine-1-carboxylate is a white crystalline solid with a molecular formula of C10H17NO3 and a molecular weight of 199.24 g/mol. Its chemical structure consists of a pyrrolidine ring with a ketone group at the 4-position, a methyl group at the 2-position, and a tert-butyl carbamate protecting group at the 1-position. The chiral center at the 2-position imparts enantiomeric purity, which is crucial for its applications in asymmetric synthesis and drug development.

In recent years, tert-butyl (2R)-2-methyl-4-oxopyrrolidine-1-carboxylate has gained considerable attention due to its potential as an intermediate in the synthesis of biologically active compounds. One notable application is in the development of inhibitors for various enzymes and receptors. For instance, this compound has been used as a key intermediate in the synthesis of inhibitors targeting protein kinases, which are involved in numerous cellular processes and are often dysregulated in diseases such as cancer and inflammatory disorders.

Research published in the Journal of Medicinal Chemistry highlights the use of tert-butyl (2R)-2-methyl-4-oxopyrrolidine-1-carboxylate in the synthesis of novel antiviral agents. These agents have shown promising activity against viral infections, including influenza and HIV. The chiral nature of this compound allows for the preparation of enantiomerically pure derivatives, which can exhibit enhanced potency and selectivity compared to their racemic counterparts.

Beyond its role in drug discovery, tert-butyl (2R)-2-methyl-4-oxopyrrolidine-1-carboxylate is also utilized in the development of agrochemicals. Its structural features make it suitable for the synthesis of pesticides and herbicides with improved efficacy and reduced environmental impact. Studies have demonstrated that derivatives of this compound can effectively control various plant pathogens while minimizing harm to non-target organisms.

The synthetic versatility of tert-butyl (2R)-2-methyl-4-oxopyrrolidine-1-carboxylate is further enhanced by its compatibility with a wide range of functional groups and reaction conditions. It can be readily modified through various chemical transformations, such as nucleophilic substitution, reduction, and coupling reactions. This flexibility makes it an attractive choice for chemists working on complex molecule syntheses.

In terms of safety and handling, tert-butyl (2R)-2-methyl-4-oxopyrrolidine-1-carboxylate is generally considered stable under standard laboratory conditions. However, it is important to follow standard safety protocols when handling this compound to ensure safe storage and use. Proper personal protective equipment (PPE) should be worn, and work should be conducted in a well-ventilated area to minimize exposure risks.

The future prospects for tert-butyl (2R)-2-methyl-4-oxopyrrolidine-1-carboxylate are promising. Ongoing research continues to explore new applications and derivatives of this compound, driven by its unique structural features and potential therapeutic benefits. As advances in synthetic methods and analytical techniques continue to evolve, it is likely that this compound will play an increasingly important role in various areas of scientific inquiry.

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