Cas no 22328-78-5 (ethyl (2S)-piperidine-2-carboxylate)

Ethyl (2S)-piperidine-2-carboxylate is a chiral ester derivative of pipecolic acid, commonly employed as a versatile intermediate in organic synthesis and pharmaceutical research. Its stereochemical purity (2S configuration) makes it particularly valuable for the preparation of enantiomerically pure compounds, including bioactive molecules and catalysts. The ethyl ester group enhances solubility in organic solvents, facilitating its use in acylation and alkylation reactions. This compound is also utilized in the synthesis of peptidomimetics and heterocyclic scaffolds. Its stability under standard conditions and compatibility with various reaction conditions underscore its utility in medicinal chemistry and asymmetric synthesis.
ethyl (2S)-piperidine-2-carboxylate structure
22328-78-5 structure
Product Name:ethyl (2S)-piperidine-2-carboxylate
CAS No:22328-78-5
MF:C8H15NO2
MW:157.210202455521
MDL:MFCD09752682
CID:843187
PubChem ID:736055
Update Time:2025-06-15

ethyl (2S)-piperidine-2-carboxylate Chemical and Physical Properties

Names and Identifiers

    • (S)-Ethyl piperidine-2-carboxylate
    • 2-Piperidinecarboxylic acid, ethyl ester, (2S)-
    • ethyl (2S)-piperidine-2-carboxylate
    • ethyl (S)-piperidine-2-carboxylate
    • SZIKRGHFZTYTIT-ZETCQYMHSA-N
    • ethyl (2S)-2-piperidinecarboxylate
    • BS-53144
    • E73989
    • EN300-866878
    • (S)-Ethylpiperidine-2-carboxylate
    • AKOS005259851
    • SCHEMBL1929065
    • DTXSID201296165
    • 22328-78-5
    • MDL: MFCD09752682
    • Inchi: 1S/C8H15NO2/c1-2-11-8(10)7-5-3-4-6-9-7/h7,9H,2-6H2,1H3
    • InChI Key: SZIKRGHFZTYTIT-UHFFFAOYSA-N
    • SMILES: CCOC(C1NCCCC1)=O

Computed Properties

  • Exact Mass: 157.11035
  • Monoisotopic Mass: 157.110278721g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 3
  • Complexity: 136
  • 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
  • XLogP3: 0.7
  • Topological Polar Surface Area: 38.3?2

Experimental Properties

  • PSA: 38.33

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Additional information on ethyl (2S)-piperidine-2-carboxylate

Introduction to Ethyl (2S)-Piperidine-2-Carboxylate (CAS No. 22328-78-5)

Ethyl (2S)-piperidine-2-carboxylate, a compound with the chemical identifier CAS No. 22328-78-5, is a significant molecule in the field of pharmaceutical chemistry and drug development. This compound belongs to the piperidine class, which is well-known for its diverse biological activities and applications in medicinal chemistry. The stereochemical configuration at the carbon-2 position, specifically the (S) configuration, plays a crucial role in determining its pharmacological properties and interactions with biological targets.

The synthesis and characterization of ethyl (2S)-piperidine-2-carboxylate have been extensively studied due to its potential as a building block in the design of novel therapeutic agents. Recent advancements in synthetic methodologies have enabled more efficient and scalable production of this compound, making it more accessible for research and development purposes. The use of chiral resolution techniques has been particularly important in ensuring the purity and enantiomeric excess of the (S)-isomer, which is often required for optimal biological activity.

One of the most compelling aspects of ethyl (2S)-piperidine-2-carboxylate is its role as a precursor in the synthesis of more complex molecules. For instance, it has been utilized in the development of protease inhibitors, which are critical in the treatment of various diseases, including HIV and cancer. The piperidine ring provides a suitable scaffold for binding to specific enzymatic targets, while the carboxylate ester group offers opportunities for further functionalization. This flexibility makes ethyl (2S)-piperidine-2-carboxylate a valuable tool for medicinal chemists.

Recent research has also highlighted the importance of ethyl (2S)-piperidine-2-carboxylate in the development of central nervous system (CNS) drugs. Piperidine derivatives are known to interact with various neurotransmitter systems, making them potential candidates for treating neurological disorders such as depression, anxiety, and epilepsy. The (S)-configuration of ethyl (2S)-piperidine-2-carboxylate has been shown to enhance its affinity for certain receptors, leading to improved therapeutic efficacy. This finding underscores the significance of stereochemistry in drug design and development.

The pharmacokinetic properties of ethyl (2S)-piperidine-2-carboxylate have also been thoroughly investigated. Studies have demonstrated that this compound exhibits good oral bioavailability and moderate metabolic stability, which are essential characteristics for a successful drug candidate. Additionally, its solubility profile has been optimized through structural modifications, improving its pharmacokinetic behavior. These attributes make ethyl (2S)-piperidine-2-carboxylate an attractive candidate for further clinical development.

In conclusion, ethyl (2S)-piperidine-2-carboxylate is a versatile and important compound in pharmaceutical chemistry. Its synthesis, stereochemistry, and biological activity have been extensively studied, providing valuable insights into its potential as a therapeutic agent. The ongoing research in this area continues to uncover new applications and opportunities for this compound, making it a cornerstone in the development of innovative drugs.

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