tert-butyl (2R)-5-oxopyrrolidine-2-carboxylate

Name: tert-butyl (2R)-5-oxopyrrolidine-2-carboxylate
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CAS No. 205524-46-5
Cat. No. CS-W003608
Molecule weight185.22
Purity≥97%
MDL No.MFCD09261417

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tert-butyl (2R)-5-oxopyrrolidine-2-carboxylate|CS-W003608

Structure of 205524-46-5

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General Information

CAS No. 205524-46-5
Cat. No. CS-W003608
Purity ≥97%
MDL No. MFCD09261417
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₅NO₃
Molecular Weight 185.22
Synonym(s) tert-butyl 5-oxo-D-prolinate
SMILES O=C([C@H]1CCC(=O)N1)OC(C)(C)C

Description

(R)-tert-Butyl 5-oxopyrrolidine-2-carboxylate is a stereochemically defined, bench-stable building block featuring a pyrrolidinone core with a tert-butyl ester handle. This configuration enables direct incorporation into asymmetric synthesis workflows, where the carbonyl group facilitates selective functionalization and the protected amine supports downstream transformations under standard conditions.

Application

(R)-tert-Butyl 5-oxopyrrolidine-2-carboxylate serves as a versatile chiral building block in synthetic organic chemistry, enabling efficient access to pyrrolidine-based scaffolds. Its oxo group at C5 facilitates selective functionalization, while the tert-butyl ester provides excellent bench stability and ease of removal under mild acidic conditions. The compound functions effectively in asymmetric synthesis, supporting diverse transformations including reductive amination, nucleophilic addition, and transition-metal-catalyzed coupling reactions.

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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Computational Chemistry Data

TPSA 55.4
LogP 0.6067
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Glutamic acid and derivatives

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

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tert-butyl (2R)-5-oxopyrrolidine-2-carboxylate

CAS No. 205524-46-5

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