(2S,4R)-1-(tert-Butoxycarbonyl)-4-(4-methylbenzyl)pyrrolidine-2-carboxylic acid

Name: (2S,4R)-1-(tert-Butoxycarbonyl)-4-(4-methylbenzyl)pyrrolidine-2-carboxylic acid
Brand: ChemScene
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CAS No. 959581-21-6
Cat. No. CS-0061301
Purity≥98%
MDL No.None

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(2S,4R)-1-(tert-Butoxycarbonyl)-4-(4-methylbenzyl)pyrrolidine-2-carboxylic acid|CS-0061301

Structure of 959581-21-6

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Description

This pyrrolidine derivative features a tert-butoxycarbonyl-protected amine and a sterically hindered 4-methylbenzyl group at C4, enabling direct incorporation into peptide sequences. The electron-rich pyrrolidine core enhances conformational rigidity, while the bench-stable protecting group facilitates straightforward deprotection under standard conditions.

Application

(2S,4R)-1-(tert-Butoxycarbonyl)-4-(4-methylbenzyl)pyrrolidine-2-carboxylic acid serves as a versatile chiral building block in medicinal chemistry, enabling efficient access to pyrrolidine-based scaffolds. The tert-butyl carbamate (Boc) group provides excellent stability and orthogonal deprotection, while the 4-methylbenzyl side chain offers robust functional group tolerance. This compound facilitates diverse transformations in peptide synthesis and heterocyclic ring construction, with reliable performance in standard bench-scale reactions.

General Information

CAS No. 959581-21-6
Cat. No. CS-0061301
Purity ≥98%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₈H₂₅NO₄
Molecular Weight 319.40
Synonym(s) N-(t-Butoxycarbonyl)-trans-4-(4-methylbenzyl)-L-proline
SMILES CC1=CC=C(C=C1)C[C@@H]2C[C@@H](C(=O)O)N(C2)C(=O)OC(C)(C)C

Computational Chemistry Data

TPSA 66.84
LogP 3.24772
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 3

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 : 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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Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Proline and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(2S,4R)-1-(tert-Butoxycarbonyl)-4-(4-methylbenzyl)pyrrolidine-2-carboxylic acid

CAS No. 959581-21-6

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