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6-((tert-Butoxycarbonyl)amino)spiro[3.3]heptane-2-carboxylic acid

  • CAS No. 1087798-38-6

  • Cat. No. CS-0050355
  • Purity≥97%
  • MDL No.MFCD11099888

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

6-((tert-Butoxycarbonyl)amino)spiro[3.3]heptane-2-carboxylic acid|CS-0050355

Structure of 1087798-38-6

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General Information

  • CAS No. 1087798-38-6
  • Cat. No. CS-0050355
  • Purity ≥97%
  • MDL No. MFCD11099888
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₂₁NO₄
  • Molecular Weight 255.31
  • Synonym(s) None
  • SMILES O=C(OC(C)(C)C)NC1CC2(C1)CC(C(=O)O)C2

Description

6-((tert-Butoxycarbonyl)amino)spiro[3.3]heptane-2-carboxylic acid features a rigid spirocyclic core that imparts conformational restraint, enhancing stereochemical control in synthesis. The tert-butoxycarbonyl group provides a stable, orthogonal amine protection strategy compatible with diverse reaction conditions. This scaffold integrates efficiently into complex molecular architectures requiring defined spatial orientation and functional group tolerance.

Application

6-((tert-Butoxycarbonyl)amino)spiro[3.3]heptane-2-carboxylic acid serves as a versatile chiral building block for the synthesis of spirocyclic scaffolds prevalent in medicinal chemistry. The tert-butyl carbamate group enables convenient protection and orthogonal deprotection, while the carboxylic acid facilitates amide coupling and conjugation. Its rigid spirocyclic core enhances conformational control, improving target selectivity in bioactive molecule development. The compound exhibits excellent bench stability and is readily purified by standard chromatographic methods.

Synthesis

  • Route1

    References

    • Journal of Organic Chemistry, , vol. 75, # 17 p. 5941 - 5952

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362-P405-P501

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Computational Chemistry Data

  • TPSA   75.63
  • LogP   2.1545
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   2

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