(R)-di-tert-Butyl 4-oxopyrrolidine-1,2-dicarboxylate

Name: (R)-di-tert-Butyl 4-oxopyrrolidine-1,2-dicarboxylate
Brand: ChemScene
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CAS No. 1260591-66-9
Cat. No. CS-0052746
Molecule weight285.34
Purity≥98%
MDL No.MFCD16875945

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(R)-di-tert-Butyl 4-oxopyrrolidine-1,2-dicarboxylate|CS-0052746

Structure of 1260591-66-9

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General Information

CAS No. 1260591-66-9
Cat. No. CS-0052746
Purity ≥98%
MDL No. MFCD16875945
Storage -20°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₂₃NO₅
Molecular Weight 285.34
Synonym(s) 1,2-di-tert-butyl (2r)-4-oxopyrrolidine-1,2-dicarboxylate
SMILES CC(C)(C)OC(=O)[C@H]1CC(=O)CN1C(=O)OC(C)(C)C

Description

(R)-di-tert-butyl 4-oxopyrrolidine-1,2-dicarboxylate features a sterically hindered pyrrolidine core with a ketone at the C4 position, enabling selective functionalization in asymmetric synthesis. The di-tert-butyl protection ensures stability and ease of handling, while the chiral center supports enantioselective transformations. This scaffold integrates readily into complex molecular architectures under standard conditions.

Application

(R)-Di-tert-butyl 4-oxopyrrolidine-1,2-dicarboxylate serves as a versatile chiral building block in asymmetric synthesis, enabling stereoselective construction of pyrrolidine and proline-derived scaffolds. The protected 4-oxopyrrolidine core facilitates reductive amination, nucleophilic addition, and transition-metal-catalyzed coupling reactions with high diastereoselectivity. Bench-stable and readily purified by flash chromatography, it functions effectively in multi-step syntheses of bioactive heterocycles and peptide mimetics.

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
Precautionary Statements : P264-P270-P280-P302+P352-P330-P362+P364-P501

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Computational Chemistry Data

TPSA 72.91
LogP 1.9066
H_Acceptors 5
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Life Science Amino Acids and their Derivatives Proline and derivatives

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(R)-di-tert-Butyl 4-oxopyrrolidine-1,2-dicarboxylate

CAS No. 1260591-66-9

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