Open AccessAsymmetric Hydrogenation vs. Resolution in the Synthesis of POSICOR®, a New Type of Calcium Antagonist
Author(s) -
Yvo Crameri,
Joseph Foricher,
Urs Hengartner,
Christian-Johannes Jenny,
Frank Kienzle,
Henri Ramuz,
Michelangelo Scalone,
Markus G. Schlageter,
Rudolf Schmid,
Shaoning Wang
Publication year - 1997
Publication title -
chimia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.387
H-Index - 55
eISSN - 2673-2424
pISSN - 0009-4293
DOI - 10.2533/chimia.1997.303
Subject(s) - mibefradil , asymmetric hydrogenation , chemistry , antagonist , catalysis , cascade , calcium , combinatorial chemistry , resolution (logic) , optically active , enantioselective synthesis , organic chemistry , chromatography , computer science , receptor , voltage dependent calcium channel , biochemistry , artificial intelligence
The pilot-plant-scale synthesis of (S)-2-(4-fluorophenyl)-3-methylbutanoic acid by asymmetric hydrogenation of 2-(4-fluorophenyl)-3-methylbut-2-enoic acid with the [Ru((R)-MeOBIPHEP)(OAc)2]-catalyst is described. The hydrogenation was performed in a continuous mode in a cascade stirred-tank reactor system at 270 bar pressure. The (S)-2-(4-fluorophenyl)-3-methylbutanoic acid is an important optically active intermediate in the synthesis of mibefradil, a new type of calcium antagonist.