Journal
ORGANIC PROCESS RESEARCH & DEVELOPMENT
Volume 21, Issue 2, Pages 208-217Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.oprd.6b00368
Keywords
MR antagonist LY2623091; Heck reaction; vinyl bromide; alaninol; Suzuki-Miyaura cross-coupling; cyanamide hydrolysis
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Funding
- Eli Lilly and Company, Lilly Research Laboratories, Indianapolis, Indiana [46285]
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A practical pilot plant convergent synthesis of MR antagonist LY2623091 was established. For synthesis convergence, a vinyl bromide geometric isomer and chiral alaninol derivative were required building blocks. Key to the synthesis route development is a stereoselective synthesis of the E-vinyl bromide via a sequential double Heck reaction, Suzuki-Miyaura cross-coupling of the vinyl bromide, a selective nitro reduction, and a highly sensitive cyanamide hydrolysis to the urea. Improvements in yield and processing were accomplished by two sets of telescoping methods which decreased the manufacturing time and provided purity enhancements.
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