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Journal of Flow Chemistry
Authors: Damien Webb and Timothy F. Jamison

Abstract

Micro Reaction Technology in Organic Synthesis. By Charlotte Wiles (Chemtrix BV, The Netherlands) and Paul Watts (Universtiy of Hull, UK). CRC Press (an imprint of Taylor & Francis Group): Boca Raton. 2011. xxii + 432 pp. $139.95. ISBN: 978-1-4398-2471-9.

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Abstract

The preparation of CpRu(MeCN)3PF6 using an easily assembled continuous flow reactor is described. This scalable, reproducible method provides the title compound in excellent yield and purity, and eliminates the need for any purification steps. Under our optimized conditions, the residence time required for complete conversion was only 5 min at an initial substrate concentration of 0.06 M, as compared to a reaction time of 12–36 h for the batch process at 0.02 M. This threefold increase in concentration and significant decrease in reaction time increases the throughput and efficiency of the synthesis. Using the simple laboratory equipment described herein, ruthenium catalyst of >99% purity was produced with a throughput of 1.56 g/h (5 mL reactor), which is 10 times the highest reported throughput for the batch process.

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Flow chemistry has attracted significant interest in pharmaceutical development, where substantial efforts have been directed toward the design of continuous processes. Here, we report a total synthesis of atropine in flow that features an unusual hydroxymethylation and separation of several byproducts with high structural similarity to atropine. Using a combination of careful pH control in three sequential liquid—liquid extractions and a functionalized resin, atropine is delivered by the flow system with >98% purity.

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The confinement of a biocatalyst designed to operate under continuous-flow conditions is a strategy developed by nature in order to achieve efficient reactions in biological media. Herein, we present a mimetic model that employs a confined lipase (CAL-B) in the production of several carboxamide derivatives from esters as precursors. The remarkable selectivity of such system is also described when α,β-unsatured carboxylic substrates are employed.

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