Description

1-Benzyl 3-ethyl 4-oxopyrrolidine-1,3-dicarboxylate (CAS No. 51814-19-8) is a high-purity synthetic intermediate with the molecular formula C₁₅H₁₇NO₅. This compound, also known by its IUPAC name 1-O-benzyl 3-O-ethyl 4-oxopyrrolidine-1,3-dicarboxylate, is a versatile building block in organic synthesis and pharmaceutical research. It features a pyrrolidine core with a ketone functionality at the 4-position and ester-protected carboxyl groups at the 1- and 3-positions, making it ideal for further derivatization. The benzyl and ethyl ester groups provide orthogonal protection strategies for selective deprotection and functionalization. This compound is supplied as a white to off-white crystalline powder with ≥95% purity (HPLC) and is rigorously tested for quality assurance. Suitable for use in medicinal chemistry, peptidomimetics, and heterocyclic synthesis, it is packaged under inert gas to ensure stability and longevity. Store at 2-8°C in a tightly sealed container to prevent moisture absorption.

Properties

• CAS Number: 51814-19-8
• Complexity: 403
• IUPAC Name: O1-benzyl O3-ethyl 4-oxopyrrolidine-1,3-dicarboxylate
• InChI: InChI=1S/C15H17NO5/c1-2-20-14(18)12-8-16(9-13(12)17)15(19)21-10-11-6-4-3-5-7-11/h3-7,12H,2,8-10H2,1H3
• InChI Key: FRNZCPLVDNHRIH-UHFFFAOYSA-N
• Exact Mass: 291.11067264
• Molecular Formula: C15H17NO5
• Molecular Weight: 291.30
• SMILES: CCOC(=O)C1CN(CC1=O)C(=O)OCC2=CC=CC=C2
• Topological: 72.9
• Monoisotopic Mass: 291.11067264
• Synonyms: 51814-19-8, 1-BENZYL 3-ETHYL 4-OXOPYRROLIDINE-1,3-DICARBOXYLATE, DTXSID50567416, DTXCID00518190, 867-377-9, ETHYL N-CBZ-4-OXOPYRROLIDINE-3-CARBOXYLATE, 1-O-benzyl 3-O-ethyl 4-oxopyrrolidine-1,3-dicarboxylate, Ethyl 1-N-Cbz-4-oxo-pyrrolidine-3-carboxylate, MFCD09878816, 4-Oxo-pyrrolidine-1,3-dicarboxylic acid 1-benzyl ester 3-ethyl ester, Ethyl 1-Cbz-4-oxopyrrolidine-3-carboxylate, 1,3-Pyrrolidinedicarboxylic acid, 4-oxo-, 3-ethyl 1-(phenylmethyl) ester, SCHEMBL3185364, FRNZCPLVDNHRIH-UHFFFAOYSA-N, AKOS015855351, CS-W003680, GS-3780, PB34472, SY003382, N-benzyloxycarbonyl-4-ethoxycarbonylpyrrolidin-3-one, 1-Benzyloxycarbonyl-4-ethoxycarbonyl-3-oxopyrrolidine, Ethyl 1-benzyloxycarbonyl-4-oxopyrrolidine-3-carboxylate, 1-Benzyl 3-ethyl 4-oxopyrrolidine-1 pound not3-dicarboxylate

Application

1-Benzyl 3-ethyl 4-oxopyrrolidine-1,3-dicarboxylate is a key intermediate in the synthesis of biologically active pyrrolidine derivatives, including protease inhibitors and CNS-targeting therapeutics. Its orthogonal ester protections enable selective modifications for structure-activity relationship (SAR) studies in drug discovery. Researchers also utilize this compound in the development of peptidomimetics and constrained scaffolds for combinatorial chemistry libraries.

Safety and Hazards

GHS Hazard Statements

• H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (50%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (50%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (50%)
• Eye Irrit. 2 (50%)
• STOT SE 3 (50%)

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