(S)-Ethyl ((3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methyl)carbamate
(S)-Ethyl ((3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methyl)carbamate, identified by CAS number 869856-10-0, is a specialized organic intermediate characterized by its rigid bicyclic benzocyclobutene framework and a carbamate functional group. This compound features two methoxy substituents on the aromatic ring and a chiral center at the 7-position, making it a valuable chiron in asymmetric synthesis. As a high-value chemical raw material, it serves as a critical structural precursor in the development of complex molecules, particularly those requiring precise stereochemical control. Its chemical stability under standard storage conditions, combined with the reactivity of the carbamate moiety, allows for versatile transformations, including reduction to the corresponding amine. In industrial and research settings, this material is handled as a technical-grade intermediate, requiring standard protective measures to ensure purity and safety. Its primary value lies in its role as a key building block for the synthesis of advanced active ingredients in the fine chemical and pharmaceutical industries.
• Advanced Pharmaceutical Synthesis: The primary application of CAS 869856-10-0 is as a key chiral intermediate in the multi-step synthesis of Ivabradine, a selective sinus node inhibitor. It provides the essential (S)-configured bicyclic amine core required for the molecule’s pharmacological profile. The carbamate group is typically reduced or hydrolyzed during the manufacturing process to yield the active amine side chain.
• Stereoselective Organic Synthesis: Due to its defined (S)-stereochemistry, this compound is utilized as a chiral building block in the construction of complex polycyclic systems. Researchers leverage the strained bicyclo[4.2.0]octa-1,3,5-triene system for specialized ring-opening or substitution reactions that maintain the integrity of the chiral center.
• Fine Chemical Production: It serves as a precursor for various derivatives in the fine chemical industry where dimethoxy-substituted benzocyclobutene motifs are required. Its structural rigidity and functional handle make it suitable for creating diverse chemical libraries for material science and drug discovery research.
• Process Optimization Research: The material is frequently used in process chemistry to refine the yields and enantiomeric purity of downstream products. Its role as a stable intermediate allows for efficient purification steps, ensuring that high-quality standards are met in large-scale industrial production cycles.
Product Name: (S)-Ethyl ((3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methyl)carbamate
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