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CS-W001157 4
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(R)-Benzyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate

  • CAS No. 72597-18-3

  • Cat. No. CS-W012891
  • Purity≥97%
  • MDL No.MFCD02683223

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

(R)-Benzyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate|CS-W012891

Structure of 72597-18-3

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General Information

  • CAS No. 72597-18-3
  • Cat. No. CS-W012891
  • Purity ≥97%
  • MDL No. MFCD02683223
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₇NO₃
  • Molecular Weight 235.28
  • Synonym(s) Z-D-Prolinol, 97
  • SMILES OC[C@@H]1N(C(OCC2=CC=CC=C2)=O)CCC1

Description

(R)-Benzyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate features a chiral pyrrolidine scaffold with a pendant hydroxymethyl group, enabling direct functionalization in asymmetric synthesis. This bench-stable derivative integrates readily into cascade reactions and serves as a key building block for bioactive alkaloid frameworks.

Application

(R)-Benzyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate serves as a versatile chiral building block for the synthesis of pyrrolidine-containing pharmaceuticals and bioactive molecules. The hydroxymethyl group enables straightforward functionalization via oxidation, protection, or coupling reactions, while the benzyl ester offers convenient deprotection under mild hydrogenolysis conditions. Its stereochemical purity supports high diastereoselectivity in downstream transformations, making it ideal for medicinal chemistry applications requiring defined stereocenters.

Synthesis

  • Route1
    • In-stock
      (R)-1-Pyrrolidin-2-ylmethanol|CS-D1509
      68832-13-3
    • null|null
      501-53-1
    • ~99%
    • In-stock
      (R)-Benzyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate|CS-W012891
      72597-18-3

    References

    • Sankyo Company, Limited Patent: EP1746095 A1, 2007 ; Location in patent: Page/Page column 79-80 ;
  • Route2

    References

    • DAIICHI PHARMACEUTICAL CO., LTD. Patent: EP1785418 A1, 2007 ; Location in patent: Page/Page column 70 ;
  • Route3

    References

    • Calveras, Jordi; Casas, Josefina; Parella, Teodor; Joglar, Jesus; Clapes, Pere Advanced Synthesis and Catalysis, 2007 , vol. 349, # 10 p. 1661 - 1666

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2810
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H319
Precautionary Statements : P264-P270-P280-P330-P405-P501

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Computational Chemistry Data

  • TPSA   49.77
  • LogP   1.7799
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   3

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