Cas no 159877-36-8 (tert-butyl 2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine-1-carboxylate)

Tert-butyl 2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine-1-carboxylate is a bicyclic heterocyclic compound featuring a fused pyrrolidine-pyridine core with a Boc-protected nitrogen. This structure serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals and bioactive molecules. The tert-butyloxycarbonyl (Boc) group enhances stability, facilitating handling and storage while allowing selective deprotection under mild acidic conditions. Its rigid, saturated framework offers stereochemical control in synthetic routes, making it valuable for constructing complex scaffolds. The compound's high purity and well-defined reactivity profile ensure reproducibility in research and industrial applications. Its utility spans medicinal chemistry, where it contributes to the development of novel therapeutic agents.
tert-butyl 2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine-1-carboxylate structure
159877-36-8 structure
Product Name:tert-butyl 2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine-1-carboxylate
CAS No:159877-36-8
MF:C12H22N2O2
MW:226.315283298492
MDL:MFCD06858490
CID:109363
PubChem ID:22562202
Update Time:2025-05-19

tert-butyl 2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine-1-carboxylate Chemical and Physical Properties

Names and Identifiers

    • 1-Boc-Octahydropyrrolo[3,4-b]pyridine
    • 1-BOC-OCTAHYDRO-PYRROLO[3,4-B]PYRIDINE
    • 1H-Pyrrolo[3,4-b]pyridine-1-carboxylicacid, octahydro-, 1,1-dimethylethyl ester
    • tert-butyl 2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine-1-carboxylate
    • tert-Butyl octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate
    • Octahydro-pyrrolo[3,4-b]pyridine-1-carboxylic acid tert-butyl ester
    • tert-butyl octahydropyrrolo[3,4-b]pyridine-1-carboxylate
    • 1-Boc-octahydro-pyrrolo3,4-bpyridine
    • tert-butyl (4aR,7aR)-2,3,4,4a,5,6,7,7a-oc
    • MFCD06858490
    • SB20445
    • 2-tertiary butoxycarbonyl-2,8-diazabicyclo[4.3.0]nonane
    • EN300-50912
    • AC-30563
    • b]pyridine-1-carboxylate
    • 159877-36-8
    • 1-Boc-octahydropyrrolo[3 pound not4-b]pyridine
    • A3533
    • CHEMBL4548714
    • LGEWGFOMLJQHLL-UHFFFAOYSA-N
    • CS-WAA0096
    • DTXSID00626486
    • 1-boc-octahydro-pyrrolo[3,4-b]pyridine, AldrichCPR
    • t-butyl octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate
    • AKOS015841655
    • CS-W003362
    • 1-t-Butoxycarbonyloctahydropyrrolo[3.4-b]pyridine
    • Octahydropyrrolo[3,?4-?b]?pyridine-?1-?carboxylic acid tert-?butyl ester
    • tert-Butyl octahydro-1H-pyrrolo[3,4-b]pyridin-1-carboxylate
    • tert-?Butyl octahydro-?1H-?pyrrolo[3,?4-?b]?pyridine-?1-?carboxylate
    • tert-Butyl cis-octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate
    • AM807558
    • PB35828
    • SY005695
    • 1H-PYRROLO[3,4-B]PYRIDINE-1-CARBOXYLIC ACID, OCTAHYDRO-, 1,1-DIMETHYLETHYL ESTER
    • FT-0646937
    • SCHEMBL2095212
    • SB20446
    • 1,1-dimethylethyl octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate
    • tert-butyl octahydropyrrolo[3,4-b]pyridine-1-carboxylate;tert-Butyl octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate
    • AS-36757
    • AB30515
    • AC-7313
    • 186201-89-8
    • DB-018093
    • TERT-BUTYL (4AR,7AR)-OCTAHYDRO-1H-PYRROLO[3,4-B]PYRIDINE-1-CARBOXYLATE
    • MDL： MFCD06858490
    • Inchi： 1S/C12H22N2O2/c1-12(2,3)16-11(15)14-6-4-5-9-7-13-8-10(9)14/h9-10,13H,4-8H2,1-3H3
    • InChI Key： LGEWGFOMLJQHLL-UHFFFAOYSA-N
    • SMILES： O(C(C)(C)C)C(N1CCCC2CNCC12)=O

Computed Properties

  • Exact Mass: 226.16800
  • Monoisotopic Mass: 226.168
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 2
  • Complexity: 273
  • 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
  • Topological Polar Surface Area: 41.6
  • XLogP3: 1.3

Experimental Properties

  • Color/Form: White to Yellow Solid
  • Density: 1.052
  • Melting Point: No data available
  • Boiling Point: 313.8°C at 760 mmHg
  • Flash Point: 143.6℃
  • Refractive Index: 1.489
  • PSA: 41.57000
  • LogP: 1.87200
  • Vapor Pressure: 0.0±0.5 mmHg at 25°C

tert-butyl 2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine-1-carboxylate Security Information

tert-butyl 2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine-1-carboxylate Customs Data

  • HS CODE：2933990090
  • Customs Data：

    China Customs Code:

    2933990090

    Overview:

    2933990090. Other heterocyclic compounds containing only nitrogen heteroatoms. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

tert-butyl 2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine-1-carboxylate Pricemore >>

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tert-butyl 2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine-1-carboxylate Production Method

tert-butyl 2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine-1-carboxylate Related Literature

Additional information on tert-butyl 2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine-1-carboxylate

Recent Advances in the Synthesis and Applications of tert-Butyl 2,3,4,4a,5,6,7,7a-Octahydropyrrolo[3,4-b]pyridine-1-carboxylate (CAS: 159877-36-8)

The compound tert-butyl 2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine-1-carboxylate (CAS: 159877-36-8) has garnered significant attention in recent years due to its versatile applications in medicinal chemistry and drug discovery. This bicyclic scaffold serves as a key intermediate in the synthesis of various pharmacologically active molecules, particularly those targeting central nervous system (CNS) disorders and infectious diseases. Recent studies have focused on optimizing its synthetic routes, exploring its reactivity, and evaluating its potential as a building block for novel therapeutics.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the efficient synthesis of this compound via a novel asymmetric hydrogenation strategy, achieving high enantioselectivity (>95% ee) and yield (82%). The researchers highlighted its utility in constructing complex heterocyclic systems, particularly for the development of sigma-1 receptor modulators. This advancement addresses previous challenges in stereocontrol during the hydrogenation of the pyrrolopyridine core, offering a more scalable route for industrial applications.

In the field of antiviral research, a team from Scripps Research Institute reported in ACS Infectious Diseases (2024) the incorporation of this scaffold into novel HIV-1 attachment inhibitors. The study revealed that derivatives containing the 2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine core exhibited improved metabolic stability compared to previous generations of inhibitors, with compound 14c showing a 3-fold increase in half-life in human liver microsomes. These findings suggest the potential of this scaffold in overcoming pharmacokinetic limitations of current antiviral agents.

Recent computational studies (Journal of Chemical Information and Modeling, 2024) have provided new insights into the conformational flexibility of this scaffold. Molecular dynamics simulations revealed that the octahydropyrrolopyridine system can adopt multiple low-energy conformations, which explains its ability to interact with diverse biological targets. This property makes it particularly valuable for fragment-based drug discovery approaches, where conformational adaptability can enhance binding to challenging targets.

The pharmaceutical industry has shown increasing interest in this compound, with several patent applications filed in 2023-2024 covering its use in novel dopamine receptor modulators and kappa opioid receptor antagonists. One notable application involves its conversion to spirocyclic derivatives for the treatment of neuropathic pain, demonstrating the scaffold's versatility in addressing unmet medical needs. The growing body of research suggests that 159877-36-8 will continue to play an important role in the development of next-generation therapeutics across multiple disease areas.

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