(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
Molecule weight243.26
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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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

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.

Synthesis

Route1
- In-stock
  
  114676-69-6
- ~84%
- In-stock
  
  256487-77-1
References
- WO2012/125887 A1, ; Page/Page column 74-75 ; WO 2012/125887 A1
Route2
- In-stock
  
  135042-17-0
- ~70%
- In-stock
  
  256487-77-1
References
- Organic Letters, , vol. 11, # 6 p. 1245 - 1248
Route3
- In-stock
  
  114676-59-4
- ~%
- In-stock
  
  256487-77-1
References
- Journal of Medicinal Chemistry, , vol. 42, # 26 p. 5426 - 5436

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-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 72.91
LogP 0.7379
H_Acceptors 5
H_Donors 0
Rotatable_Bonds 1

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

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

CAS No. 256487-77-1

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