Author
Schmid Christopher Randall
Bio: Schmid Christopher Randall is an academic researcher from Eli Lilly and Company. The author has contributed to research in topics: Raloxifene & Allylic rearrangement. The author has an hindex of 12, co-authored 31 publications receiving 537 citations.
Topics: Raloxifene, Allylic rearrangement, Nucleophile, Heteroatom, Zatosetron
Papers
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203 citations
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TL;DR: Two different continuous flow approaches to a key 1H-4-substituted imidazole intermediate are reported, highlighting the rapid development of chemistry in research-scale PFRs and speed to material delivery through linear scale up to a pilot- scale PFR under GMP conditions.
61 citations
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TL;DR: In this article, the synthesis of two novel glyceraldehyde surrogates, 2,3-O-(3-pentylidene)-D-glyceral dehyde (2) and 3-pentanone-derived protecting group facilitates the extraction of product from aqueous oxidation solutions.
Abstract: The synthesis of two novel glyceraldehyde surrogates, 2,3-O-(3-pentylidene)-D-glyceraldehyde (2) and 2,3-O-(3-pentylidene)-L-glyceraldehyde (3) is presented. Synthesis, handling and storage advantages of 2 and 3 over the conventionally employed 2,3-O-isopropylidene-D-glyceraldehyde (1) are discussed. The 3-pentanone-derived protecting group facilitates the extraction of product from aqueous oxidation solutions, while the 3-pentanone liberated on ketal deprotection can be efficiently removed at reduced pressures
40 citations
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TL;DR: In this article, the authors report the first literature report of the use of this classic demethylation chemistry on multikilogram scale, including the adaptation of this chemistry to 22-L and pilot-plant scale.
33 citations
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TL;DR: In this paper, a modified benzo[b]thiophene-based selective estrogen receptor modulator (SERM) raloxifene (Evista®) is presented.
30 citations
Cited by
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TL;DR: There have been parallel and collaborative exchanges between academic research and industrial developments since the materials were first reported in 1914, it is demonstrated.
Abstract: In contrast to a recently expressed, and widely cited, view that “Ionic liquids are starting to leave academic labs and find their way into a wide variety of industrial applications”, we demonstrate in this critical review that there have been parallel and collaborative exchanges between academic research and industrial developments since the materials were first reported in 1914 (148 references)
4,865 citations
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TL;DR: Privileged substructures are believed to achieve this through the mimicry of common protein surface elements that are responsible for binding, such as β- and gamma;-turns.
Abstract: Privileged substructures are of potentially great importance in medicinal chemistry. These scaffolds are characterized by their ability to promiscuously bind to a multitude of receptors through a variety of favorable characteristics. This may include presentation of their substituents in a spatially defined manner and perhaps also the ability to directly bind to the receptor itself, as well as exhibiting promising characteristics to aid bioavailability of the overall molecule. It is believed that some privileged substructures achieve this through the mimicry of common protein surface elements that are responsible for binding, such as β- and gamma;-turns. As a result, these structures represent a promising means by which new lead compounds may be identified.
2,620 citations
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TL;DR: This review introduces readers to the basic principles and fundamentals of flow chemistry and critically discusses recent flow chemistry accounts.
Abstract: Flow chemistry involves the use of channels or tubing to conduct a reaction in a continuous stream rather than in a flask Flow equipment provides chemists with unique control over reaction parameters enhancing reactivity or in some cases enabling new reactions This relatively young technology has received a remarkable amount of attention in the past decade with many reports on what can be done in flow Until recently, however, the question, “Should we do this in flow?” has merely been an afterthought This review introduces readers to the basic principles and fundamentals of flow chemistry and critically discusses recent flow chemistry accounts
1,192 citations
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TL;DR: This Review discusses recent literature examples of continuous-flow organic synthesis where hazardous reactions or extreme process windows have been employed, with a focus on applications of relevance to the preparation of pharmaceuticals.
Abstract: In the past few years, continuous-flow reactors with channel dimensions in the micro- or millimeter region have found widespread application in organic synthesis. The characteristic properties of these reactors are their exceptionally fast heat and mass transfer. In microstructured devices of this type, virtually instantaneous mixing can be achieved for all but the fastest reactions. Similarly, the accumulation of heat, formation of hot spots, and dangers of thermal runaways can be prevented. As a result of the small reactor volumes, the overall safety of the process is significantly improved, even when harsh reaction conditions are used. Thus, microreactor technology offers a unique way to perform ultrafast, exothermic reactions, and allows the execution of reactions which proceed via highly unstable or even explosive intermediates. This Review discusses recent literature examples of continuous-flow organic synthesis where hazardous reactions or extreme process windows have been employed, with a focus on applications of relevance to the preparation of pharmaceuticals.
1,059 citations
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606 citations