With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.204512-95-8,(S)-Tetrahydrofuran-3-amine hydrochloride,as a common compound, the synthetic route is as follows.
A ?Personal Chemistry? microwave vial is charged with the title compound of (300 mg, 0.73 mmol), (S)-3-aminotetrahydrofuran hydrochloride (360 mg, 2.9 mmol), palladium (II) acetate (8 mg, 5 mol %), 1,1′-bis(diphenylphosphino)ferrocene (DPPF) (40 mg, 10 mol %), and sodium tert-butoxide (210 mg, 2.19 mmol). To this is added toluene (5 mL) and the reaction is heated with microwave irradiation to 115 C. for 30 min. After allowing the reaction vessel to cool, a suspension formed and is filtered and the filtrate evaporated. The residue is purified by flash chromatography, and the intermediate product (162 mg, 53%) is hydrolyzed by dissolution in 25% dimethylsulfoxide/ethanol, adding 1 N NaOH (0.25 mL) and 30% aqueous hydrogen peroxide (0.25 mL), followed by stirring at room temperature for 1 hours. An off yellow precipitate formed and H2O is added to precipitate more solids. The solids are collected by vacuum to yield of (S)-4-(6,6-dimethyl-4-oxo-3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indol-1-yl)-2-(tetrahydrofuran-3-ylamino)benzamide (102 mg, 60% yield) as an off yellow powder. LC/MS: m/z=436 [M+H]-. 1H NMR (400 MHz, d6 DMSO): delta 8.56 (d, 1H), 7.97 (bs, 1H), 7.75 (d, 1H), 7.69 (s, 1H), 7.31 (bs, 1H), 6.73 (s, 1H), 6.65 (dd, 1H), 4.16 (m, 1H), 3.85 (m, 1H), 3.82 (m, 1H), 3.71 (m, 1H), 3.53 (dd, 1H), 2.74 (s, 2H), 2.33 (s, 2H), 1.73 (m, 1H), 0.99 (s, 6H)., 204512-95-8
The synthetic route of 204512-95-8 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; Huang, Kenneth He; Ommen, Andy J.; Barta, Thomas E.; Hughes, Philip F.; Veal, James; Ma, Wei; Smith, Emilie D.; Woodward, Angela R.; McCall, W. Stephen; US2008/269193; (2008); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem