ChemicalBook CAS DataBase List Siponimod

Siponimod synthesis

13synthesis methods

Product Name:Siponimod
CAS Number:916806-97-8
Molecular formula:C14H15F3O2
Molecular Weight:272.26

4-(cyclohex-1-en-1-yl)-3-(trifluoromethyl)benzoic acid

1034188-31-2
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916806-97-8
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Yield: 88%

Reaction Conditions:

with palladium on activated charcoal;hydrogen in methanol at 50; under 7600.51 Torr; for 72 h;

Steps:

1.6 Step 6 (0264) (0265) [00250] 4-cyclohexyl-3-(trifluoromethyl)benzoic acid
Step 6 (0264) (0265) [00250] 4-cyclohexyl-3-(trifluoromethyl)benzoic acid: To a solution of 4-(cyclohex-1-en- 1-yl)-3-(trifluoromethyl)benzoic acid (6.4 g, 23.68 mmol, 1.00 equiv.) in methanol (60 mL), Pd/C (0.64 g) was added. The resulting solution was stirred for 72 h at 50 ^oC with an inert atmosphere of H₂ (10 atm.). The reaction mixture was cooled. The solids were filtered out. The resulting mixture was concentrated under vacuum to afford 5.7 g (88%) of 4-cyclohexyl- 3-(trifluoromethyl) benzoic acid as a white solid. LC-MS: m/z = 271 [M-H]-.

References:

AUSPEX PHARMACEUTICALS, INC.;ZHANG, Chengzhi;CHAKMA, Justin WO2017/120124, 2017, A1 Location in patent:Paragraph 00249-00250