Large-Scale Synthesis and Modifications of Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acid (BCP)

doi:10.1021/acs.joc.1c00977

Paper

Large-Scale Synthesis and Modifications of Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acid (BCP)

Published Jun 24, 2021 · Vasyl Ripenko, D. Vysochyn, Ivan Klymov

The Journal of Organic Chemistry

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1

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Abstract

In flow photochemical addition of propellane to diacetyl allowed construction of the bicyclo[1.1.1]pentane (BCP) core in a 1 kg scale within 1 day. Haloform reaction of the formed diketone in batch afforded bicyclo[1.1.1]pentane-1,3-dicarboxylic acid in a multigram amount. Representative gram scale transformations of the diacid were also performed to obtain various BCP-containing building blocks—alcohols, acids, amines, trifluoroborates, amino acids, etc.—for medicinal chemistry.

Study Snapshot

Large-scale synthesis of bicyclo[1.1.1]pentane-1,3-dicarboxylic acid (BCP) using in flow photochemical addition of propellane to diacetyl in 1 day enables various BCP-containing building blocks for medicinal chemistry.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Large-Scale Synthesis and Modifications of Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acid (BCP)

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References

Citations

CF3-Cyclobutanes: Synthesis, Properties, and Evaluation as a Unique tert-Butyl Group Analogue

The 1-trifluoromethyl-cyclobutyl group can preserve bioactivity and enhance resistance to metabolic clearance in bioactive compounds, despite slightly larger steric size and increased lipophilicity.

Highlights of the Recent Patent Literature: Continuous Chemistry in the Pharmaceutical Industry

Continuous chemistry in the pharmaceutical industry enables difficult-to-scale chemistries or provides significant process intensification without needing journal articles.

Visible-Light-Driven Decarboxylative Borylation: Rapid Access to α- and β-Amino-boronamides.

Visible-light-induced decarboxylative borylation efficiently produces - and -amino-boronamides in moderate to excellent yields, offering scalable synthesis of DAN boronates.

Strain-Release Photocatalysis.

Strain-release photocatalysis allows for the creation of unique chemical architectures under mild conditions, offering potential for future synthetic advancements.

Synthesis of Bicyclo[1.1.0]butanes from Iodo-Bicyclo[1.1.1]pentanes.

This study presents a two-step process for synthesizing substituted bicyclo[1.1.0]butanes using iodo-bicyclo[1.1.1]pentanes under metal-free conditions at room temperature.

Preparation of bicyclo[1.1.1]pentane-derived nucleoside analogues

Bicyclo[1.1.1]pentane-derived nucleoside analogues, including pyrimidine, purine, and C-nucleoside analogues, can be prepared in 1-5 steps with good yields for drug discovery.