Cas no 191347-94-1 (tert-butyl (3R)-3-formylpyrrolidine-1-carboxylate)

Technical Introduction: tert-Butyl (3R)-3-formylpyrrolidine-1-carboxylate is a chiral building block widely used in organic synthesis and pharmaceutical research. Its key advantages include a stereochemically defined (R)-configuration at the 3-position, which is critical for enantioselective synthesis. The tert-butoxycarbonyl (Boc) protecting group enhances stability and facilitates selective deprotection under mild acidic conditions. The formyl moiety provides a versatile handle for further functionalization, such as reductive amination or nucleophilic addition. This compound is particularly valuable in the preparation of bioactive molecules, including peptidomimetics and heterocyclic scaffolds. High purity and consistent stereochemical integrity make it a reliable intermediate for complex synthetic routes.
tert-butyl (3R)-3-formylpyrrolidine-1-carboxylate structure
191347-94-1 structure
Product Name:tert-butyl (3R)-3-formylpyrrolidine-1-carboxylate
CAS No:191347-94-1
MF:C10H17NO3
MW:199.246883153915
MDL:MFCD14635728
CID:2093014
PubChem ID:1514342
Update Time:2025-05-23

tert-butyl (3R)-3-formylpyrrolidine-1-carboxylate Chemical and Physical Properties

Names and Identifiers

    • (R)-tert-Butyl 3-formylpyrrolidine-1-carboxylate
    • (3R)-3-Formyl-1-pyrrolidinecarboxylic acid tert-butyl ester
    • (R)-1-Boc-3-pyrrolidinecarbaldehyde
    • (R)-3-formylpyrrolidine-1-carboxylic acid tert-butyl ester
    • (R)-3-forMyl-1-Boc-pyrrolidine
    • R-1-Boc-3-pyrrolidinecarbaldehyde
    • tert-butyl (3R)-3-forMylpyrrolidine-1-carboxylate
    • 1-Pyrrolidinecarboxylic acid, 3-forMyl-, 1,1-diMethylethyl ester, (R)-
    • DWLADVOODHZCFV-MRVPVSSYSA-N
    • CS-0048573
    • 191347-94-1
    • (3R)-1-Boc-3-formylpyrrolidine
    • DTXSID00974792
    • EN300-1697197
    • SCHEMBL935410
    • 1-Pyrrolidinecarboxylic acid, 3-formyl-, 1,1-dimethylethyl ester, (3R)-
    • AS-42180
    • tert-butyl (R)-3-formylpyrrolidine-1-carboxylate
    • (R)-3-Formylpyrrolidine-1-carboxylic Acid t-Butyl Ester
    • (R)-tert-butyl3-formylpyrrolidine-1-carboxylate
    • AKOS024262357
    • tert-butyl (3R)-3-formylpyrrolidine-1-carboxylate
    • MDL: MFCD14635728
    • Inchi: InChI=1S/C10H17NO3/c1-10(2,3)14-9(13)11-5-4-8(6-11)7-12/h7-8H,4-6H2,1-3H3/t8-/m1/s1
    • InChI Key: DWLADVOODHZCFV-MRVPVSSYSA-N
    • SMILES: CC(C)(C)OC(=O)N1CC[C@H](C1)C=O

Computed Properties

  • Exact Mass: 199.121
  • Monoisotopic Mass: 199.121
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 4
  • Complexity: 232
  • 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: 46.6A^2
  • XLogP3: 0.7

Experimental Properties

  • Density: 1.148
  • Boiling Point: 276.3 °C at 760 mmHg
  • Flash Point: 120.9 °C
  • PSA: 46.61000
  • LogP: 1.38020

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Additional information on tert-butyl (3R)-3-formylpyrrolidine-1-carboxylate

Introduction to tert-butyl (3R)-3-formylpyrrolidine-1-carboxylate (CAS No. 191347-94-1)

tert-butyl (3R)-3-formylpyrrolidine-1-carboxylate, with the CAS number 191347-94-1, is a specialized organic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal biology. This compound belongs to the pyrrolidine class, characterized by a five-membered heterocyclic structure containing one nitrogen atom. The presence of a formyl group and a tert-butyl ester moiety enhances its utility in synthetic chemistry, particularly in the development of chiral intermediates and bioactive molecules.

The structure of tert-butyl (3R)-3-formylpyrrolidine-1-carboxylate features a stereochemically defined (3R) configuration at the pyrrolidine ring, which is crucial for its biological activity. This stereochemistry influences its interactions with biological targets, making it a valuable building block in drug discovery. The formyl group serves as a reactive handle for further functionalization, enabling the synthesis of more complex molecules such as peptidomimetics and protease inhibitors.

In recent years, there has been growing interest in the application of tert-butyl (3R)-3-formylpyrrolidine-1-carboxylate in the design of novel therapeutic agents. Its unique structural features make it particularly suitable for modulating enzyme activity and receptor binding. For instance, researchers have explored its potential in developing inhibitors targeting enzymes involved in inflammatory pathways, such as cyclooxygenases and lipoxygenases. The tert-butyl ester group provides stability while allowing for selective hydrolysis under physiological conditions, enhancing its pharmacological profile.

One of the most compelling aspects of tert-butyl (3R)-3-formylpyrrolidine-1-carboxylate is its role in enantioselective synthesis. The (3R) configuration ensures that derived compounds exhibit high enantiomeric purity, which is critical for achieving optimal pharmacological efficacy and minimizing side effects. This has led to its incorporation into several clinical trials where enantiopure compounds are essential for therapeutic success. The compound’s ability to serve as a chiral precursor has also been leveraged in the synthesis of non-proteinogenic amino acids, expanding the arsenal of molecular tools available to medicinal chemists.

Advances in computational chemistry have further enhanced the utility of tert-butyl (3R)-3-formylpyrrolidine-1-carboxylate. Molecular modeling studies have demonstrated its potential binding interactions with various biological targets, providing insights into its mechanism of action. These studies often involve docking simulations to predict how the compound might interact with enzymes or receptors at an atomic level. Such computational approaches have accelerated the discovery process by allowing researchers to screen large libraries of derivatives before conducting expensive experimental validations.

The synthesis of tert-butyl (3R)-3-formylpyrrolidine-1-carboxylate itself represents a significant achievement in organic chemistry. Traditional methods often involve multi-step sequences requiring careful control over reaction conditions to achieve high yields and enantiomeric purity. However, recent innovations in catalytic asymmetric synthesis have streamlined these processes, making it more feasible to produce this compound on an industrial scale. These advancements not only improve efficiency but also reduce costs associated with drug development.

In conclusion, tert-butyl (3R)-3-formylpyrrolidine-1-carboxylate (CAS No. 191347-94-1) is a versatile and highly valuable compound in pharmaceutical research. Its unique structural features and stereochemical properties make it an indispensable tool for developing novel therapeutics targeting various diseases. As research continues to uncover new applications for this molecule, its importance in medicinal chemistry is only expected to grow.

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