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CS-W001157 4
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2-tert-butyl 6-methyl 3,4-dihydroisoquinoline-2,6(1H)-dicarboxylate

  • CAS No. 170097-66-2

  • Cat. No. CS-W018407
  • Purity≥97%
  • MDL No.None

*For research and further manufacturing use only, not for direct human use.

2-tert-butyl 6-methyl 3,4-dihydroisoquinoline-2,6(1H)-dicarboxylate|CS-W018407

Structure of 170097-66-2

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General Information

  • CAS No. 170097-66-2
  • Cat. No. CS-W018407
  • Purity ≥97%
  • MDL No. None
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₆H₂₁NO₄
  • Molecular Weight 291.34
  • Synonym(s) None
  • SMILES COC(=O)c1ccc2CN(CCc2c1)C(=O)OC(C)(C)C

Description

This 2-tert-butyl 6-methyl 3,4-dihydroisoquinoline-2,6(1H)-dicarboxylate features a sterically shielded dihydroisoquinoline core with dual ester functionalities. The tert-butyl and methyl groups enhance solubility and stability, while the electron-rich heterocyclic scaffold enables efficient coupling in synthetic sequences. This compound serves as a robust intermediate for complex alkaloid architectures.

Application

2-tert-Butyl 6-methyl 3,4-dihydroisoquinoline-2,6(1H)-dicarboxylate serves as a versatile scaffold for the synthesis of isoquinoline-based heterocycles, enabling efficient functionalization at both nitrogen and aromatic positions. Its protected dihydroisoquinoline core exhibits excellent bench stability and compatibility with standard coupling reactions, facilitating access to complex alkaloid-like architectures and API intermediates through selective deprotection and cyclization strategies.

Synthesis

  • Route1

    References

    • JANSSEN PHARMACEUTICA N.V. Patent: WO2008/109336 A1, 2008 ; Location in patent: Page/Page column 39 ; WO 2008/109336 A1
  • Route2
    • null|null
      18107-18-1
    • In-stock
      2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid|CS-W005911
      170097-67-3
    • ~%
    • In-stock
      2-tert-butyl 6-methyl 3,4-dihydroisoquinoline-2,6(1H)-dicarboxylate|CS-W018407
      170097-66-2

    References

    • WO2012/122340 A1, ; Page/Page column 59-60 ;
  • Route3
    • null|null
      67-56-1
    • null|null
      201230-82-2
    • tert-Butyl 6-(trifluoromethylsulfonyloxy)-3,4-dihydroisoquinoline-2(1H)-carboxylate|CS-M1348
      158984-84-0
    • ~65%
    • In-stock
      2-tert-butyl 6-methyl 3,4-dihydroisoquinoline-2,6(1H)-dicarboxylate|CS-W018407
      170097-66-2

    References

    • Haginoya, Noriyasu; Kobayashi, Syozo; Komoriya, Satoshi; Yoshino, Toshiharu; Suzuki, Makoto; Shimada, Takashi; Watanabe, Kengo; Hirokawa, Yumiko; Furugori, Taketoshi; Nagahara, Takayasu Journal of Medicinal Chemistry, 2004 , vol. 47, # 21 p. 5167 - 5182

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H320-H335
Precautionary Statements : P261-P280-P302+P352

Quality Control

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Computational Chemistry Data

  • TPSA   55.84
  • LogP   2.7664
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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