(2R,4R)-1-(tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid

Name: (2R,4R)-1-(tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid
Brand: ChemScene
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CAS No. 158567-91-0
Cat. No. CS-0181061
Purity≥97%
MDL No.MFCD09952342

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(2R,4R)-1-(tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid|CS-0181061

Structure of 158567-91-0

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General Information

CAS No. 158567-91-0
Cat. No. CS-0181061
Purity ≥97%
MDL No. MFCD09952342
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₆H₂₁NO₄
Molecular Weight 291.34
Synonym(s) 1,2-Pyrrolidinedicarboxylic acid, 4-phenyl-, 1-(1,1-dimethylethyl) ester, (2R-trans)- (9CI)
SMILES O=C([C@@H]1N(C(OC(C)(C)C)=O)C[C@@H](C2=CC=CC=C2)C1)O

Description

This chiral pyrrolidine derivative features a tert-butoxycarbonyl-protected amine and a phenyl-substituted C4 position, enabling direct incorporation into peptide backbones. The stereochemistry at the 2R,4R centers ensures predictable conformational behavior in foldamers and constrained peptides. Bench-stable and moisture-tolerant, it streamlines synthesis of non-natural amino acid building blocks for medicinal chemistry campaigns.

Application

(2R,4R)-1-(tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid serves as a stereochemically defined building block for the synthesis of bioactive pyrrolidine-containing scaffolds. The Boc group enables straightforward deprotection under mild acidic conditions, while the phenyl and carboxylic acid functionalities offer versatile handles for further functionalization. Its stability and compatibility with standard coupling protocols make it ideal for peptide and medicinal chemistry applications requiring controlled stereochemistry and modular side-chain elaboration.

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362

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Computational Chemistry Data

TPSA 66.84
LogP 2.8642
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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(2R,4R)-1-(tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid

CAS No. 158567-91-0

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