Yuki Saito, Ken Nishizawa, Benjamin Laroche, Haruro Ishitani, Shū Kobayashi
Angewandte Chemie (International ed. in English) 2022 Mar 21We describe the continuous-flow synthesis of (R)-tamsulosin, a blockbuster therapeutic drug employed for dysuria associated with urinary stones and benign prostatic hyperplasia, by utilizing sequential heterogeneous catalysis. Two heterogeneous catalysts have been developed for the synthesis, and the key step involves reductive amination of nitriles using dimethylpolysilane-modified Pd on activated carbon/calcium phosphate. Overall, (R)-tamsulosin was obtained in 60 % yield and 64 % ee (99 % ee after recrystallization) in a flow stream through four catalytic transformations without the need for the isolation or purification of any intermediates or byproduct. © 2022 Wiley-VCH GmbH.
Yuki Saito, Ken Nishizawa, Benjamin Laroche, Haruro Ishitani, Shū Kobayashi. Continuous-Flow Synthesis of (R)-Tamsulosin Utilizing Sequential Heterogeneous Catalysis. Angewandte Chemie (International ed. in English). 2022 Mar 21;61(13):e202115643
PMID: 35068027
View Full Text