tert-Butyl (R)-4-amino-3,3-difluoropyrrolidine-1-carboxylate

Name: tert-Butyl (R)-4-amino-3,3-difluoropyrrolidine-1-carboxylate
Brand: ChemScene
Availability: InStock
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CAS No. 2199214-47-4
Cat. No. CS-0380577
Purity≥98%
MDL No.None

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tert-Butyl (R)-4-amino-3,3-difluoropyrrolidine-1-carboxylate|CS-0380577

Structure of 2199214-47-4

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General Information

CAS No. 2199214-47-4
Cat. No. CS-0380577
Purity ≥98%
MDL No. None
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₆F₂N₂O₂
Molecular Weight 222.23
Synonym(s) 1-Pyrrolidinecarboxylic acid, 4-amino-3,3-difluoro-, 1,1-dimethylethyl ester, (4R)-
SMILES CC(C)(C)OC(N1C[C@H](C(F)(C1)F)N)=O

Description

tert-Butyl (R)-4-amino-3,3-difluoropyrrolidine-1-carboxylate delivers a chiral, electron-deficient pyrrolidine scaffold with enhanced metabolic stability. The tert-butyl ester facilitates handling and purification, while the 3,3-difluoro substitution imparts conformational rigidity and improved membrane permeability. This building block integrates efficiently into peptidomimetics and bioactive small molecules.

Application

tert-Butyl (R)-4-amino-3,3-difluoropyrrolidine-1-carboxylate serves as a stereochemically defined building block for the synthesis of fluorinated pyrrolidine scaffolds. The tert-butyl carbamate group provides stability and facilitates straightforward deprotection under mild acidic conditions. The 3,3-difluoro substitution enhances metabolic stability and modulates basicity, while the primary amine enables diverse functionalization, including acylation, alkylation, and incorporation into peptide-like motifs via standard coupling protocols.

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

Quality Control

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Computational Chemistry Data

TPSA 55.56
LogP 1.1997
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Functional Group Fluoride

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Key Words

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tert-Butyl (R)-4-amino-3,3-difluoropyrrolidine-1-carboxylate

CAS No. 2199214-47-4

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