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Palladium-Catalyzed C–O Coupling of a Sterically Hindered Secondary Alcohol with an Aryl Bromide and Significant Purity Upgrade in the API Step
10.1021/acs.oprd.8b00022 2018-04-12 The final two steps used to prepare greater than 1 kg of a compound evaluated as a treatment for type 2 diabetes are reported. The application of a palladium-catalyzed C–O coupling presented significant challenges due to the nature of the reactants, impuritie... |
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UV PhotoVap: Demonstrating How a Simple and Versatile Reactor Based on a Conventional Rotary Evaporator Can Be Used for UV Photochemistry
10.1021/acs.oprd.8b00037 2018-04-12 We report the use of a simple rotary evaporator as a semi-continuous UV photochemical reactor. By generation of a thin film from the rotation of a flask, better light penetration is achieved, and in this work we used high-power Hg lamps to enable the direct i... |
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Novel Process for Preparation of Tetrabenazine and Deutetrabenazine
10.1021/acs.oprd.8b00011 2018-04-10 A novel process for the synthesis of tetrabenazine (1) and deutetrabenazine (2), two well-known drugs used for the treatment of chorea associated with Huntington’s disease, has been developed. All of the reaction parameters were optimized through a series of ... |
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Ir-Catalyzed Borylation as an Efficient Route to a Nicotine Hapten
10.1021/acs.oprd.8b00053 2018-04-09 The process development of a nicotine analog or hapten (1) for conjugation to a protein as an antigen is described. The original process in early development used an Ir-catalyzed borylation reaction to enable rapid derivatization of nicotine with the desired ... |
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Crystallization of a Metastable Solvate and Impact of the Isolation Method on the Material Properties of the Anhydrous Product
10.1021/acs.oprd.8b00062 2018-04-09 We report the crystallization of a metastable small-molecule solvate and the effect of the isolation method on the physical and material properties of the resulting anhydrous material. The anhydrous crystalline products obtained from two different isolation r... |
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Synthetic Strategies toward SGLT2 Inhibitors
10.1021/acs.oprd.8b00017 2018-04-09 Gliflozins are an important class of prescription drugs used to treat type II diabetes. They reduce blood sugar levels by targeting the sodium-glucose transport protein 2 (SGLT2) and consequently inhibit glucose reabsorption in the kidney. There are currently... |
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On-Demand Generation and Consumption of Diazomethane in Multistep Continuous Flow Systems
10.1021/acs.oprd.7b00302 2018-04-03 Diazomethane is an exceptionally versatile C1 building block in organic synthesis. However, reactions involving the use of diazomethane impose significant challenges for safe scale-up. This review aims to highlight the recent developments in processes and equ... |
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Recent Developments in the Reduction of Aromatic and Aliphatic Nitro Compounds to Amines
10.1021/acs.oprd.6b00205 2018-03-30 The reduction of the nitro group represents a powerful and widely used transformation that allows to introducing an amino group in the molecule. New synthetic strategies for complex functionalized molecular architectures are deeply needed, including highly ef... |
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Exemplifying Prediction of Preferred Coupling Partners in Developing a Buchwald–Hartwig Coupling for the Synthesis of a c-Kit Inhibitor
10.1021/acs.oprd.8b00043 2018-03-29 Two convergent syntheses for compound 1 are described that apply Buchwald–Hartwig coupling as the key step. This development work provides a direct comparison of the coupling results from different coupling partners and illustrates that more efficiency can be... |
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A Short Review on Synthetic Advances toward the Synthesis of Rufinamide, an Antiepileptic Drug
10.1021/acs.oprd.7b00373 2018-03-29 Chronic neurological disorder of the brain is the main reason for the disease epilepsy, which affects people of almost all ages. According to World Health Organization estimates, particularly in developing regions of the world nearly 80% of people suffer from... |