1-(Tert-butoxycarbonyl)-5,5-dimethylpyrrolidine-2-carboxylic acid

Name: 1-(Tert-butoxycarbonyl)-5,5-dimethylpyrrolidine-2-carboxylic acid
Brand: ChemScene
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CAS No. 900158-99-8
Cat. No. CS-0154802
Purity≥97%
MDL No.MFCD13190739

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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1-(Tert-butoxycarbonyl)-5,5-dimethylpyrrolidine-2-carboxylic acid|CS-0154802

Structure of 900158-99-8

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General Information

CAS No. 900158-99-8
Cat. No. CS-0154802
Purity ≥97%
MDL No. MFCD13190739
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₂₁NO₄
Molecular Weight 243.30
Synonym(s) Boc-5,5-dimethyl-DL-Pro-OH
SMILES CC(C)(C)OC(=O)N1C(CCC1(C)C)C(=O)O

Description

This protected pyrrolidine carboxylic acid features a sterically hindered diastereoselective scaffold with a tert-butoxycarbonyl group that enables stable, high-yield coupling in peptide synthesis. The dimethyl substitution enhances conformational rigidity and resistance to racemization under standard conditions.

Application

1-(Tert-butoxycarbonyl)-5,5-dimethylpyrrolidine-2-carboxylic acid serves as a stable, bench-ready building block for the synthesis of pyrrolidine-based scaffolds. The tert-butyl carbamate (Boc) group enables straightforward protection and deprotection under mild acidic conditions, while the geminal dimethyl substitution enhances conformational rigidity and metabolic stability. This compound facilitates efficient amide coupling and cyclization reactions, making it particularly valuable in the construction of cyclic peptides and bioactive heterocycles.

Synthesis

Route1
- In-stock
  
  24424-99-5
- 146954-59-8
- ~88%
- In-stock
  
  900158-99-8
References
- Alonso De Diego, Sergio A.; Gutierrez-Rodriguez, Marta; Perez de Vega, M. Jesus; Gonzalez-Muniz, Rosario; Herranz, Rosario; Martin-Martinez, Mercedes; Cenarruzabeitia, Edurne; Frechilla, Diana; Rio, Joaquin Del; Jimeno, M. Luisa; Garcia-Lopez, M. Teresa Bioorganic and Medicinal Chemistry Letters, 2006 , vol. 16, # 13 p. 3396 - 3400

Safety Information

Download SDS

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-P280-P302+P352

Quality Control

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Computational Chemistry Data

TPSA 66.84
LogP 2.2491
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Boc

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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1-(Tert-butoxycarbonyl)-5,5-dimethylpyrrolidine-2-carboxylic acid

CAS No. 900158-99-8

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