Practical synthesis of (S)-2-(4-fluorophenyl)-3-methylbutanoic acid, key building block for the calcium antagonist Mibefradil
Publication type: Journal Article
Publication date: 1997-11-01
Catalysis
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
A short, technically feasible route was developed for the synthesis of (S)2-(4-fluorophenyl)-3-methylbutanoic acid (S)- 2 with an overall yield of 80% starting from 4-fluorophenylacetic acid. Asymmetric hydrogenation of the easily accessible unsaturated acid 3 in the presence of ruthenium(II) carboxylato complexes containing chiral atropisomeric diphosphines afforded (S)- 2 in up to 94% ee. The ee of (S)- 2 was upgraded to 98% by crystallization of its sodium salt. The same protocol was also applied to the synthesis of (S)-2-(4-chlorophenyl)-3-methylbutanoic acid.
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34
Total citations:
34
Citations from 2024:
3
(8.82%)
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Crameri Y. et al. Practical synthesis of (S)-2-(4-fluorophenyl)-3-methylbutanoic acid, key building block for the calcium antagonist Mibefradil // Tetrahedron Asymmetry. 1997. Vol. 8. No. 21. pp. 3617-3623.
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Crameri Y., Foricher J., Scalone M., Schmid R. Practical synthesis of (S)-2-(4-fluorophenyl)-3-methylbutanoic acid, key building block for the calcium antagonist Mibefradil // Tetrahedron Asymmetry. 1997. Vol. 8. No. 21. pp. 3617-3623.
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RIS
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TY - JOUR
DO - 10.1016/S0957-4166(97)00498-9
UR - https://doi.org/10.1016/S0957-4166(97)00498-9
TI - Practical synthesis of (S)-2-(4-fluorophenyl)-3-methylbutanoic acid, key building block for the calcium antagonist Mibefradil
T2 - Tetrahedron Asymmetry
AU - Crameri, Yvo
AU - Foricher, Joseph
AU - Scalone, Michelangelo
AU - Schmid, R.
PY - 1997
DA - 1997/11/01
PB - Elsevier
SP - 3617-3623
IS - 21
VL - 8
SN - 0957-4166
SN - 1362-511X
ER -
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BibTex (up to 50 authors)
Copy
@article{1997_Crameri,
author = {Yvo Crameri and Joseph Foricher and Michelangelo Scalone and R. Schmid},
title = {Practical synthesis of (S)-2-(4-fluorophenyl)-3-methylbutanoic acid, key building block for the calcium antagonist Mibefradil},
journal = {Tetrahedron Asymmetry},
year = {1997},
volume = {8},
publisher = {Elsevier},
month = {nov},
url = {https://doi.org/10.1016/S0957-4166(97)00498-9},
number = {21},
pages = {3617--3623},
doi = {10.1016/S0957-4166(97)00498-9}
}
Cite this
MLA
Copy
Crameri, Yvo, et al. “Practical synthesis of (S)-2-(4-fluorophenyl)-3-methylbutanoic acid, key building block for the calcium antagonist Mibefradil.” Tetrahedron Asymmetry, vol. 8, no. 21, Nov. 1997, pp. 3617-3623. https://doi.org/10.1016/S0957-4166(97)00498-9.