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ChemicalBook CAS DataBase List Almotriptan
154323-57-6

Almotriptan synthesis

8synthesis methods
-

Yield: 92%

Reaction Conditions:

with nickel dichloride;lithium tert-butoxide;nixantphos in tetrahydrofuran at 0 - 80; for 13 h;Inert atmosphere;Reagent/catalyst;

Steps:

1 Example 1, synthesis of Almotriptan comprising the steps of:
Under argon, was added in dry Schlenk flask (Schlenk bottle) of NiCl2 (25.9mg, 0.2mmol), and dried under vacuum for 2h, anhydrous tetrahydrofuran (5mL) and phosphine ligand (132.4mg, 0.24mmol), stirred at room temperature for 1h, and NiCl2 phosphine ligand molar equivalent ratio of 6: 5. Then the above mixture was added t-butoxide (320.0mg, 4.0mmol), stirred at room temperature and the reaction temperature was lowered to 0 , pyrrolidine was added dropwise methyl sulfonamide (298.4mg, 2.0mmol) and Commercialization 3,5-substituted indole bromides (641.3mg, 2.4mmol), the ratio of phosphine ligand and methyl pyrrolidine is 3:25 sulfonamide, sulfonamide-methyl pyrrolidine and lithium t-butoxide molar when the ratio of 1: 2, pyrrolidine methyl sulfonamide and 3,5-substituted indole bromides molar equivalent ratio of 5: 6.After stirring the reaction continued at 80 12h, quenched with saturated aqueous ammonium chloride was added the reaction, the reaction solution (2mL × 4) and extracted with ethyl acetate, the organic layers combined, dried over anhydrous sodium sulfate, concentrated and then purified by column chromatography gel (n-hexane / ethyl acetate 1: 2) to give a solid almotriptan (654.0mg, 92% yield), purity 95%.

References:

China Agricultural University;Zheng, Bing;Gao, Gui;Chen, Xiangzhu;Zhang, Yuanyuan;Hou, Shicong;Wang, Min CN105503693, 2016, A Location in patent:Paragraph 0041; 0042; 0043; 0044; 0045; 0046; 0047; 0048

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