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

Name: (R)-1-tert-Butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate
Brand: ChemScene
Availability: InStock
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CAS No. 256487-77-1
Cat. No. CS-W005221
Purity≥97%
MDL No.MFCD09954936

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(R)-1-tert-Butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate|CS-W005221

Structure of 256487-77-1

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Description

(R)-1-tert-Butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate features a stereodefined pyrrolidine core with orthogonal protecting groups, enabling selective functionalization in asymmetric synthesis. The tert-butyl and methyl esters provide stability and compatibility with diverse reaction conditions, while the enone functionality serves as a key electrophilic handle for C–C bond formation. This scaffold is particularly valuable in the construction of complex nitrogen-containing heterocycles and natural product analogs.

Application

(R)-1-tert-Butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate serves as a versatile chiral building block in asymmetric synthesis, enabling the construction of pyrrolidine-based scaffolds with defined stereochemistry. The molecule's bench-stable nature, combined with orthogonal functionality—particularly the tert-butyl ester and oxo group—facilitates selective transformations in multistep sequences. It functions effectively in standard coupling reactions and serves as a key intermediate in the synthesis of bioactive heterocycles and medicinal chemistry leads.

General Information

CAS No. 256487-77-1
Cat. No. CS-W005221
Purity ≥97%
MDL No. MFCD09954936
Storage -20°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₇NO₅
Molecular Weight 243.26
Synonym(s) N-Boc-4-oxo-L-proline methyl ester
SMILES O=C(N1[C@@H](C(OC)=O)CC(C1)=O)OC(C)(C)C

Computational Chemistry Data

TPSA 72.91
LogP 0.7379
H_Acceptors 5
H_Donors 0
Rotatable_Bonds 1

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 Functional Group Ester

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

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)-1-tert-Butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate

CAS No. 256487-77-1

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