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(R)-1-N-Boc-beta-proline

  • CAS No. 72925-16-7

  • Cat. No. CS-B0422
  • Purity≥97%
  • MDL No.MFCD03094727

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

(R)-1-N-Boc-beta-proline|CS-B0422

Structure of 72925-16-7

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General Information

  • CAS No. 72925-16-7
  • Cat. No. CS-B0422
  • Purity ≥97%
  • MDL No. MFCD03094727
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₇NO₄
  • Molecular Weight 215.25
  • Synonym(s) (R)-1-tert-Butoxycarbonyl-pyrrolidine-3-carboxylic acid
  • SMILES O=C(OC(C)(C)C)N(CC1)C[C@@H]1C(O)=O

Description

(R)-1-N-Boc-beta-proline is a bench-stable, moisture-tolerant chiral building block featuring a protected amine and a rigid pyrrolidine ring. This configuration enables selective incorporation into peptide sequences and asymmetric synthesis, where its defined stereochemistry ensures high diastereoselectivity in coupling reactions.

Application

(R)-1-N-Boc-β-proline serves as a stable, bench-ready chiral building block for the synthesis of peptidomimetics and bioactive heterocycles. Its protected amine and carboxylic acid functionalities enable direct incorporation into SPPS workflows and facilitate efficient cyclization reactions. The Boc group ensures excellent stability during storage and handling, while enabling selective deprotection under mild acidic conditions. Functions effectively in coupling reactions with diverse nucleophiles and serves as a key scaffold in the construction of constrained β-amino acid derivatives.

Synthesis

  • Route1

    References

    • Murphy, John A.; Tripoli, Regis; Khan, Tanweer A.; Mali, Umesh W. Organic Letters, 2005 , vol. 7, # 15 p. 3287 - 3289
  • Route2

    References

    • European Journal of Organic Chemistry, , # 4 p. 673 - 682
  • Route3

    References

    • European Journal of Organic Chemistry, , # 4 p. 673 - 682

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS09
Signal Word : Warning
UN#: 3077
Class : 9
Packing Group : Ⅲ
Hazard Statements : H400
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   66.84
  • LogP   1.328
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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