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tert-Butyl 2,4-dioxopyrrolidine-1-carboxylate

  • CAS No. 182352-59-6

  • Cat. No. CS-0035557
  • Purity≥95%
  • MDL No.MFCD18914399

*For research and further manufacturing use only, not for direct human use.

tert-Butyl 2,4-dioxopyrrolidine-1-carboxylate|CS-0035557

Structure of 182352-59-6

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General Information

  • CAS No. 182352-59-6
  • Cat. No. CS-0035557
  • Purity ≥95%
  • MDL No. MFCD18914399
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₃NO₄
  • Molecular Weight 199.20
  • Synonym(s) 2,4-Dioxo-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester
  • SMILES O=C(N1C(CC(C1)=O)=O)OC(C)(C)C

Description

tert-Butyl 2,4-dioxopyrrolidine-1-carboxylate serves as a stable, bench-compatible synthon for constructing nitrogen-containing heterocycles. This masked pyrrolidinone derivative features a readily cleavable tert-butyl ester and two carbonyl groups positioned at C2 and C4, enabling selective functionalization in complex molecule synthesis. The electron-deficient ring system facilitates nucleophilic addition reactions under mild conditions.

Application

tert-Butyl 2,4-dioxopyrrolidine-1-carboxylate serves as a stable, bench-ready synthon for the construction of pyrrolidine-based scaffolds. Its diketone functionality enables selective enolization and alkylation, facilitating the synthesis of substituted pyrrolidines with defined stereochemistry. The tert-butoxycarbonyl (Boc) group offers orthogonal protection and mild deprotection under acidic conditions, enhancing utility in multi-step sequences. This reagent is particularly valuable in medicinal chemistry for building core structures in bioactive molecules.

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   63.68
  • LogP   0.7229
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   0

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