Journal
ORGANIC PROCESS RESEARCH & DEVELOPMENT
Volume 20, Issue 2, Pages 446-451Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.oprd.5b00322
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The development of a continuous process for the thermal Overman rearrangement of O-[(2R,3S)-2-(tert-butyldimethylsilyloxymethyl)-3,6-dihydro-2H-pyran-3-yl]-trichloro-ethanecarboximidate 3 to the corresponding trichloroacetamide 4 is described. Trichloroacetimidate 4 is an intermediate for an active pharmaceutical intermediate (API) under development at Actelion Pharmaceuticals Ltd. The instability of compounds 3 and 4 at temperatures above 100 degrees C prevented scale-up of the original batch mode procedure to the required multikilogram scale. This problem was solved by developing a flow chemistry process used for the successful production of 95 kg of 4.
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