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CS-W001157 4
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Methyl (2S,4R)-1-(tert-butoxycarbonyl)-4-aminopyrrolidine-2-carboxylate

  • CAS No. 121148-00-3

  • Cat. No. CS-M1798
  • Purity≥97%
  • MDL No.MFCD01861782

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

Methyl (2S,4R)-1-(tert-butoxycarbonyl)-4-aminopyrrolidine-2-carboxylate|CS-M1798

Structure of 121148-00-3

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General Information

  • CAS No. 121148-00-3
  • Cat. No. CS-M1798
  • Purity ≥97%
  • MDL No. MFCD01861782
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₂₀N₂O₄
  • Molecular Weight 244.29
  • Synonym(s) trans-4-Amino-1-Boc-2-pyrrolidinecarboxylic acid methyl ester
  • SMILES O=C(OC)[C@H]1N(C(OC(C)(C)C)=O)C[C@H](N)C1

Description

Methyl (2S,4R)-1-(tert-butoxycarbonyl)-4-aminopyrrolidine-2-carboxylate is a chiral pyrrolidine derivative featuring a protected amine and ester functionality. This scaffold integrates a stereodefined amino group flanked by a tert-butoxycarbonyl (Boc) protection, enabling selective transformations in peptide synthesis and medicinal chemistry workflows. The methyl ester moiety offers enhanced solubility and stability under standard conditions, facilitating downstream derivatization.

Application

Methyl (2S,4R)-1-(tert-butoxycarbonyl)-4-aminopyrrolidine-2-carboxylate serves as a key chiral building block for pyrrolidine-based scaffolds in medicinal chemistry. The Boc-protected amine and ester functionalities enable sequential transformations, including deprotection, coupling, and cyclization reactions. Its stereochemical integrity supports reproducible synthesis of complex heterocycles, while the tert-butyl carbamate group offers stability and ease of purification under standard bench conditions.

Synthesis

  • Route1
    • null|null
      121147-97-5
    • ~51%
    • In-stock
      Methyl (2S,4R)-1-(tert-butoxycarbonyl)-4-aminopyrrolidine-2-carboxylate|CS-M1798
      121148-00-3

    References

    • Torino, Domenica; Mollica, Adriano; Pinnen, Francesco; Feliciani, Federica; Spisani, Susanna; Lucente, Gino Bioorganic and Medicinal Chemistry, 2009 , vol. 17, # 1 p. 251 - 259
  • Route2
    • null|null
      84520-68-3
    • ~%
    • In-stock
      Methyl (2S,4R)-1-(tert-butoxycarbonyl)-4-aminopyrrolidine-2-carboxylate|CS-M1798
      121148-00-3

    References

    • US2008/306086 A1, ; Page/Page column 11-12; 28 ; US 20080306086 A1
  • Route3

    References

    • Bioorganic and Medicinal Chemistry, , vol. 10, # 5 p. 1399 - 1415

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   81.86
  • LogP   0.4961
  • H_Acceptors   5
  • H_Donors   1
  • Rotatable_Bonds   1

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