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tert-Butyl 5-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate

  • CAS No. 216064-48-1

  • Cat. No. CS-0040928
  • Purity≥95%
  • MDL No.MFCD08275037

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

tert-Butyl 5-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate|CS-0040928

Structure of 216064-48-1

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General Information

  • CAS No. 216064-48-1
  • Cat. No. CS-0040928
  • Purity ≥95%
  • MDL No. MFCD08275037
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₉NO₃
  • Molecular Weight 249.31
  • Synonym(s) tert-butyl 5-hydroxy-3,4-dihydro-1H-isoquinoline-2-carboxylate
  • SMILES O=C(N1CC2=C(C(O)=CC=C2)CC1)OC(C)(C)C

Description

tert-Butyl 5-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate features a hydroxylated dihydroisoquinoline scaffold with a bench-stable tert-butyl ester protecting group. This compound serves as a key intermediate in the synthesis of complex isoquinoline alkaloids and bioactive heterocycles, offering enhanced solubility and stability during multi-step transformations.

Application

tert-Butyl 5-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate serves as a versatile intermediate in the synthesis of isoquinoline-based scaffolds. The hydroxyl group enables selective derivatization, while the tert-butyl ester offers stability and ease of removal under mild acidic conditions. It functions effectively in palladium-catalyzed coupling reactions and facilitates the construction of medicinally relevant heterocycles through standard functional group interconversions.

Synthesis

  • Route1

    References

    • Takeda Chemical Industries, Ltd. Patent: EP1123918 A1, 2001 ;
  • Route2

    References

    • Watanabe, Toshihiro; Kinoyama, Isao; Takizawa, Kenji; Hirano, Seiko; Shibanuma, Tadao Chemical and Pharmaceutical Bulletin, 1999 , vol. 47, # 5 p. 672 - 677
  • Route3

    References

    • Fray, M. Jonathan; Allen, Paul; Bradley, Paul R.; Challenger, Clare E.; Closier, Michael; Evans, Tim J.; Lewis, Mark L.; Mathias, John P.; Nichols, Carly L.; Po-Ba, Yvonne M.; Snow, Hayley; Stefaniak, Mark H.; Vuong, Hannah V. Tetrahedron, 2006 , vol. 62, # 29 p. 6869 - 6875

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-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   49.77
  • LogP   2.6854
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   0

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