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tert-Butyl 2-hydroxypyrrolidine-1-carboxylate

  • CAS No. 84766-91-6

  • Cat. No. CS-D0581
  • Purity≥95%
  • MDL No.MFCD09031185

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

tert-Butyl 2-hydroxypyrrolidine-1-carboxylate|CS-D0581

Structure of 84766-91-6

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General Information

  • CAS No. 84766-91-6
  • Cat. No. CS-D0581
  • Purity ≥95%
  • MDL No. MFCD09031185
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₇NO₃
  • Molecular Weight 187.24
  • Synonym(s) N-Boc-Pyrrolidin-2-Ol
  • SMILES OC1CCCN1C(OC(C)(C)C)=O

Description

tert-Butyl 2-hydroxypyrrolidine-1-carboxylate features a hydroxylated pyrrolidine core protected by a tert-butoxycarbonyl group, offering enhanced stability and solubility in polar organic solvents. This scaffold integrates readily into complex molecular architectures, serving as a key intermediate in asymmetric synthesis and medicinal chemistry. The pendant hydroxyl group enables further derivatization via oxidation or coupling reactions.

Application

tert-Butyl 2-hydroxypyrrolidine-1-carboxylate serves as a versatile pyrrolidine scaffold building block, enabling efficient access to functionalized heterocycles through standard transformations. The hydroxyl group provides a handle for selective derivatization, while the tert-butyl carbamate offers robust protection under acidic and basic conditions. Its bench stability and ease of purification make it well-suited for iterative synthesis in medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • Yoshitomi, Yayoi; Arai, Hiromi; Makino, Kazuishi; Hamada, Yasumasa Tetrahedron, 2008 , vol. 64, # 51 p. 11568 - 11579
  • Route2

    References

    • Kokotos, Christoforos G.; Aggarwal, Varinder K. Chemical Communications, 2006 , # 20 p. 2156 - 2158
  • Route3
    • null|null
      201230-82-2
    • In-stock
      tert-Butyl allylcarbamate|CS-W007444
      78888-18-3
    • ~%
    • In-stock
      tert-Butyl 2-hydroxypyrrolidine-1-carboxylate|CS-D0581
      84766-91-6

    References

    • Schmidt, Axel M.; Eilbracht, Peter Organic and Biomolecular Chemistry, 2005 , vol. 3, # 12 p. 2333 - 2343

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   1.3357
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   0

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