Ethyl 4-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethoxy]-3-oxobutanoate
Ethyl 4-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethoxy]-3-oxobutanoate, identified by CAS number 88150-75-8, is a specialized organic intermediate widely utilized in the fine chemical and pharmaceutical industries. This compound is characterized by its complex structure, which incorporates a phthalimide-protected amino-ethoxy group attached to an ethyl acetoacetate derivative. As a functionalized beta-keto ester, it exhibits significant reactivity suitable for various condensation and cyclization reactions. In an industrial context, it is valued for its role in the multi-step synthesis of cardiovascular agents, particularly those belonging to the dihydropyridine class. The molecule’s design allows for the precise introduction of specific side chains during the construction of heterocyclic frameworks. Proper handling involves maintaining stable environmental conditions, as the ester and keto functionalities are sensitive to extreme pH and moisture. It serves as a high-value building block for researchers and manufacturers focused on complex organic synthesis and active pharmaceutical ingredient (API) development.
• Synthesis of Dihydropyridines: The primary application of CAS 88150-75-8 is as a key intermediate in the production of Amlodipine and its derivatives. It provides the essential side chain required for the calcium channel blocker’s pharmacological profile.
• Hantzsch Multi-Component Reaction: This compound acts as a vital precursor in the Hantzsch synthesis, where it reacts with aldehydes and nitrogen sources to form the 1,4-dihydropyridine core. The beta-keto ester moiety is specifically designed for these cyclization processes.
• Amine Protection Strategy: The presence of the 1,3-dioxoisoindoline (phthalimide) group serves as a robust protecting group for the primary amine. This allows the molecule to undergo various chemical transformations without side reactions at the nitrogen center, with the amine being liberated in the final stages of synthesis.
• Medicinal Chemistry Research: Beyond large-scale API manufacturing, the compound is used in R&D settings to develop novel heterocyclic compounds and analogs for cardiovascular research, leveraging its unique ether-linked phthalimido structure.
Product Name: Ethyl 4-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethoxy]-3-oxobutanoate
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