Photo-oxidation of Cyclopentadiene Using Continuous Processing: Application to the Synthesis of (1<i>R</i>,4<i>S</i>)-4-Hydroxycyclopent-2-en-1-yl Acetate
E. Herrero-Gómez, Cornelis H. M. van der Loo, Lena Huck, Ana Rioz‐Martínez, Nandell F. Keene, Bryan Li, Kees Pouwer, Christophe Allais
Abstract
(1R,4S)-4-Hydroxycyclopent-2-en-1-yl acetate is a chiral small building block that was requested to advance several Pfizer programs into the clinic. Pfizer and Syncom partnered to develop a photo-oxidation process of cyclopentadiene using a flow approach followed by subsequent bis-acetylation of the meso diol and final biocatalytic desymmetrization. This continuous process was demonstrated on a 6 g·h–1 input and is amenable to larger scale. The optimization and scale-up of this sequence is described therein.
Topics & Concepts
CyclopentadieneDesymmetrizationContinuous flowBlock (permutation group theory)ChemistryProcess (computing)Sequence (biology)Flow chemistryCombinatorial chemistryOrganic chemistryComputer scienceEnantioselective synthesisMathematicsCatalysisEngineeringBiochemistryCombinatoricsBiochemical engineeringOperating systemInnovative Microfluidic and Catalytic Techniques InnovationOxidative Organic Chemistry ReactionsRadical Photochemical Reactions