1-Methyl-5-oxo-3-pyrrolidinecarboxylic acid methyl ester

1-Methyl-5-oxo-3-pyrrolidinecarboxylic acid methyl ester (CAS 59857-86-2) is a versatile organic building block that has gained significant attention as a multifunctional intermediate in pharmaceutical R&D, drug discovery, and heterocyclic chemistry. As a fragment molecule, Methyl 1-methyl-5-oxopyrrolidine-3-carboxylate serves as a key scaffold for molecular splicing, expansion, and modification, and provides a structural foundation for the design and screening of new drug candidates.

In medicinal chemistry, 1-Methyl-5-oxo-3-pyrrolidinecarboxylic acid methyl ester as a structural anchor for developing drug-like molecules targeting intractable diseases. This compound has been incorporated into transdermal patches for ondansetron delivery, indicating its utility in pharmaceutical formulations aimed at treating chemotherapy-induced nausea, and has shown activity in bromodomain studies, binding to the active site of bromodomain 1 and inhibiting the activity of acetamide, a potent bromodomain 1 inhibitor [2†L6-L9]. Furthermore, Methyl 1-methyl-5-oxopyrrolidine-3-carboxylate has demonstrated broad-spectrum biological potential, including antioxidant properties that protect cells from oxidative stress, neuroprotective effects for conditions like Alzheimer’s disease, and significant anticancer activity via its derivatives against A549 lung adenocarcinoma cells, showing structure-dependent anticancer activity when tested using MTT assays .

In the broader field of organic synthesis, 1-Methyl-5-oxo-3-pyrrolidinecarboxylic acid methyl ester as a vital intermediate in the production of pharmaceuticals, agrochemicals, and specialty chemicals.

Product Parameters

Why Cosperpharm? – Our Competitive Advantages

Synthetic Routes

The synthesis of Methyl 1-methyl-5-oxopyrrolidine-3-carboxylate is well-established and can be accomplished via the following documented approaches:

Method 1: Through 1-Methyl-5-oxo-3-pyrrolidinecarboxylic Acid (Standard Route)

Synthesize the corresponding carboxylic acid via cyclization of appropriate precursors, then esterify with methanol using a strong acid catalyst (e.g., H₂SO₄) or a coupling reagent (e.g., DCC).

Method 2: Direct from Dimethyl Itaconate and Methylamine (Higher Yield Route, ~92%)

React dimethyl itaconate (fumarate ester derivative) with methylamine; cyclization proceeds via Michael addition and amidation to provide Methyl 1-methyl-5-oxopyrrolidine-3-carboxylate in approximately 92% yield.

Method 3: Industrial-Scale Process

Industrial production often adopts continuous flow reactors with automated systems to optimize reaction temperature, pressure, and catalyst use, ensuring consistent product quality and yield. The final purification is typically achieved through distillation under reduced pressure (160–161 °C at 18 Torr) or recrystallization.

Frequently Asked Questions (FAQ)

Q1: What are the primary applications of 1-Methyl-5-oxo-3-pyrrolidinecarboxylic acid methyl ester?

A: It is primarily used as a fragment scaffold in drug discovery, enabling molecular splicing and expansion for designing novel drug candidates. It also has applications in transdermal formulations, bromodomain research, antioxidant studies, and antimicrobial development.

Q2: What biological activities have been reported?

A: This compound exhibits antioxidant activity (protects cells from oxidative stress), neuroprotective effects (potential for neurodegenerative diseases like Alzheimer’s), anticancer activity (significant cytotoxicity against A549 lung adenocarcinoma cells), and antimicrobial properties against Gram-positive bacteria and drug-resistant fungal strains.

Contact Us

Let‘s discuss how Cosperpharm can support your next project.Thank you for considering Cosperpharm as your trusted partner for Methyl 1-methyl-5-oxopyrrolidine-3-carboxylate (CAS 59857-86-2). We look forward to hearing from you and providing the quality products and responsive service you deserve.