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CS-W001157 4
Total: USD 88.00

1-Boc-(S)-4-Methylenepyrrolidine-2-carboxylic acid

  • CAS No. 84348-38-9

  • Cat. No. CS-0009247
  • Purity≥97%
  • MDL No.MFCD01861787

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

1-Boc-(S)-4-Methylenepyrrolidine-2-carboxylic acid|CS-0009247

Structure of 84348-38-9

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General Information

  • CAS No. 84348-38-9
  • Cat. No. CS-0009247
  • Purity ≥97%
  • MDL No. MFCD01861787
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₇NO₄
  • Molecular Weight 227.26
  • Synonym(s) N-Boc-4-methylene-L-proline
  • SMILES O=C([C@H](C1)N(C(OC(C)(C)C)=O)CC1=C)O

Description

1-Boc-(S)-4-Methylenepyrrolidine-2-carboxylic acid is a stereochemically defined, bench-stable building block featuring a pyrrolidine core with a strategically positioned methylene group and a Boc-protected carboxylic acid. This configuration enables direct incorporation into complex heterocyclic scaffolds and facilitates efficient diversification in medicinal chemistry campaigns.

Application

1-Boc-(S)-4-Methylenepyrrolidine-2-carboxylic acid serves as a versatile chiral building block for the synthesis of pyrrolidine-containing scaffolds. Its protected amine and exocyclic methylene group enable efficient functionalization, facilitating C–C bond formation and heterocycle construction under standard coupling conditions. The Boc group provides bench stability and simplifies purification, while the (S)-configuration ensures stereochemical fidelity in downstream transformations relevant to medicinal chemistry and process development.

Synthesis

  • Route1
    • null|null
      1779-49-3
    • In-stock
      N-Boc-4-oxo-L-proline|CS-M1682
      84348-37-8
    • ~64%
    • In-stock
      1-Boc-(S)-4-Methylenepyrrolidine-2-carboxylic acid|CS-0009247
      84348-38-9

    References

    • ENANTA PHARMACEUTICALS, INC.; QIU, Yao-Ling; PENG, Xiaowen; KIM, In, Jong; CAO, Hui; TANG, Datong; OR, Yat, Sun; WANG, Guoqiang; XU, Guoyou Patent: WO2012/158861 A2, 2012 ; Location in patent: Page/Page column 19-20 ;
  • Route2

    References

    • Manfre; Kern; Biellmann Journal of Organic Chemistry, 1992 , vol. 57, # 7 p. 2060 - 2065
  • Route3
    • null|null
      144422-81-1
    • ~%
    • In-stock
      1-Boc-(S)-4-Methylenepyrrolidine-2-carboxylic acid|CS-0009247
      84348-38-9

    References

    • Tetrahedron, , vol. 48, # 31 p. 6529 - 6536

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

Quality Control

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Computational Chemistry Data

  • TPSA   66.84
  • LogP   1.6366
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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