Cas no 1523617-90-4 (tert-Butyl 6-hydroxy-3-azabicyclo[3.1.1]heptane-3-carboxylate)

Tert-Butyl 6-hydroxy-3-azabicyclo[3.1.1]heptane-3-carboxylate is a bicyclic tertiary alcohol ester with a rigid azabicyclo[3.1.1]heptane scaffold, serving as a valuable intermediate in pharmaceutical synthesis. The hydroxyl group at the 6-position enhances its reactivity for further functionalization, while the tert-butyloxycarbonyl (Boc) protecting group ensures stability during synthetic manipulations. Its constrained ring structure contributes to stereochemical control in the preparation of bioactive compounds, particularly in the development of CNS-targeting molecules. The compound's balanced lipophilicity and polarity make it suitable for medicinal chemistry applications, including the synthesis of analogs with improved pharmacokinetic properties. Careful handling is recommended due to potential sensitivity to acidic or basic conditions that may cleave the Boc group.
tert-Butyl 6-hydroxy-3-azabicyclo[3.1.1]heptane-3-carboxylate structure
1523617-90-4 structure
Product Name:tert-Butyl 6-hydroxy-3-azabicyclo[3.1.1]heptane-3-carboxylate
CAS No:1523617-90-4
MF:C11H19NO3
MW:213.273463487625
MDL:MFCD17168421
CID:2093722
PubChem ID:72207318
Update Time:2025-10-30

tert-Butyl 6-hydroxy-3-azabicyclo[3.1.1]heptane-3-carboxylate Chemical and Physical Properties

Names and Identifiers

    • tert-Butyl 6-hydroxy-3-azabicyclo[3.1.1]heptane-3-carboxylate
    • AKOS025146815
    • PB15310
    • 3-azabicyclo[3.1.1]heptane-3-carboxylic acid, 6-hydroxy-, 1,1-dimethylethyl ester
    • DB-189440
    • (1R,5S,6R)-rel-3-Boc-6-hydroxy-3-azabicyclo[3.1.1]heptane
    • DTXSID901159443
    • 1,1-Dimethylethyl 6-hydroxy-3-azabicyclo[3.1.1]heptane-3-carboxylate
    • FIPZGKLMWFRNLL-UHFFFAOYSA-N
    • 3-azabicyclo[3.1.1]heptane-3-carboxylicacid,6-hydroxy-,1,1-dimethylethylester
    • 1357353-36-6
    • EN300-1168688
    • 3-Boc-3-azabicyclo[3.1.1]heptane-6-ol
    • 6-HYDROXY-3-AZABICYCLO[3.1.1]HEPTANE-3-CARBOXYLIC ACID 1,1-DIMETHYLETHYL ESTER
    • 1523617-90-4
    • MFCD22209399
    • SY103464
    • CS-0154766
    • SCHEMBL17630406
    • AS-42898
    • 6-Hydroxy-3-azabicyclo[3.1.1]heptane-3-carboxylic acid, 1,1-dimethylethyl ester
    • HEC35336
    • MDL: MFCD17168421
    • Inchi: 1S/C11H19NO3/c1-11(2,3)15-10(14)12-5-7-4-8(6-12)9(7)13/h7-9,13H,4-6H2,1-3H3
    • InChI Key: FIPZGKLMWFRNLL-UHFFFAOYSA-N
    • SMILES: OC1C2CN(C(=O)OC(C)(C)C)CC1C2

Computed Properties

  • Exact Mass: 213.13649347g/mol
  • Monoisotopic Mass: 213.13649347g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 3
  • Complexity: 260
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 2
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 0.9
  • Topological Polar Surface Area: 49.8?2

tert-Butyl 6-hydroxy-3-azabicyclo[3.1.1]heptane-3-carboxylate Pricemore >>

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Additional information on tert-Butyl 6-hydroxy-3-azabicyclo[3.1.1]heptane-3-carboxylate

Comprehensive Overview of tert-Butyl 6-hydroxy-3-azabicyclo[3.1.1]heptane-3-carboxylate (CAS No. 1523617-90-4)

The compound tert-Butyl 6-hydroxy-3-azabicyclo[3.1.1]heptane-3-carboxylate (CAS No. 1523617-90-4) is a highly specialized bicyclic organic molecule that has garnered significant attention in pharmaceutical and synthetic chemistry research. Its unique azabicyclo[3.1.1]heptane core structure, combined with the tert-butyl carboxylate and hydroxy functional groups, makes it a versatile intermediate for drug discovery and development. Researchers are particularly interested in its potential applications in central nervous system (CNS) therapeutics, owing to its structural similarity to bioactive alkaloids.

In recent years, the demand for tert-Butyl 6-hydroxy-3-azabicyclo[3.1.1]heptane-3-carboxylate has surged due to its role in synthesizing novel small-molecule inhibitors and protease-targeting drugs. The compound’s bicyclic scaffold is a key feature for achieving high binding affinity in enzyme inhibition, a topic frequently searched in AI-driven drug design platforms. Its hydroxy group at the 6-position also allows for further derivatization, enabling the creation of libraries for high-throughput screening (HTS).

From an industrial perspective, the synthesis of CAS No. 1523617-90-4 involves multi-step organic reactions, including Boc protection and ring-closing strategies. These processes are often optimized for scalability, a hot topic in green chemistry forums. The compound’s stability under various pH conditions further enhances its utility in prodrug formulations, a trending subject in pharmacokinetics research.

Another area of interest is the compound’s potential in neurodegenerative disease research. Given the rising global focus on Alzheimer’s and Parkinson’s therapies, the 3-azabicyclo[3.1.1]heptane moiety is being explored for its ability to cross the blood-brain barrier (BBB). This aligns with frequent search queries like “BBB-permeable scaffolds” and “CNS drug delivery systems” in academic databases.

Quality control of tert-Butyl 6-hydroxy-3-azabicyclo[3.1.1]heptane-3-carboxylate is critical, with analytical techniques such as HPLC, NMR, and mass spectrometry ensuring purity. These methods are commonly discussed in AI-powered literature reviews, reflecting the compound’s importance in precision medicine. Additionally, its chiral centers pose challenges in stereoselective synthesis, a niche yet growing field in asymmetric catalysis.

In summary, CAS No. 1523617-90-4 represents a cutting-edge building block in medicinal chemistry, bridging gaps between synthetic feasibility and therapeutic innovation. Its relevance to drug discovery, green synthesis, and CNS targeting ensures its continued prominence in both academic and industrial research.

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