Introduction of a new synthetic route about 3-Amino-3-(4-fluorophenyl)propan-1-ol

At the same time, in my other blogs, there are other synthetic methods of this type of compound,612532-52-2, 3-Amino-3-(4-fluorophenyl)propan-1-ol, and friends who are interested can also refer to it.

Adding a certain compound to certain chemical reactions, such as: 612532-52-2, 3-Amino-3-(4-fluorophenyl)propan-1-ol, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Recommanded Product: 3-Amino-3-(4-fluorophenyl)propan-1-ol, blongs to alcohols-buliding-blocks compound. Recommanded Product: 3-Amino-3-(4-fluorophenyl)propan-1-ol

Preparation of 3-amino-3-(4-fluorophenyl)-1-propanesulfonic acid; A solution of borane:tetrahydrofurane complex (1M, 100 mL) was added dropwise over 1 hour to a cold (0 C.) suspension of DL-3-amino-3-(4-fluorophenyl)propionoc acid (7.30 g, 39.9 mmol) in THF (40 mL). The mixture was heated to reflux for 22 hours. The mixture was then cooled to 0 C. and methanol (35 mL) was added over 15 minutes. The mixture was then heated to reflux for 30 minutes and concentrated to a thick oil. The oil was coevaporated 3 times with methanol (50 mL). The crude product was used directly in next step. The oil that was obtained in the previous step was dissolved in water and added dropwise to concentrated HBr (44 mL) The solution was heated at reflux for 18 hours. It was then concentrated to dryness (11.58 g). The solid was suspended in hot heptane/2-butanone then cooled to room temperature. Ether was added and the mixture was stirred for 30 minutes. The solid was collected by filtration and rinsed with ether (9.97 g, about 66% for two steps). The 3-bromo-1-(4-fluorophenyl)-1-propylamine hydrobromide (obtained in step 2, 32 mmol) was added to a solution of sodium sulfite (3.78 g, 30 mmol) in water (40 mL). The mixture was heated at 90 C. for 2.5 hours, and was then concentrated to a thick paste. Concentrated HCl (8 mL) was added to the paste. The resulting suspension was stirred for 20 minutes at room temperature. The solid was collected by filtration and rinsed with concentrated HCl (3×30 mL). The filtrated solid was concentrated to dryness. The solid was washed in ethanol/toluene then dried in vacuo (3.79 g). The solid was recrystallized in ethanol (25 mL) and water (6 mL). After cooling to room temperature, the solid was collected by filtration, rinsed with ethanol (2×5 mL) and dried overnight at 60 C. in a vacuum oven. The title compounds was obtained as a fine white crystalline solid, yield 2.37 g, 26% overall yield. 1H NMR 1H (500 MHz, D2O) delta 2.22-2.36 (m, 2H), 2.54-2.60 (m, 1H), 2.65-2.71(m, 1H), 4.37-4.40 (m, 1H), 7.07 (t, J=8.5 Hz, 2H), 7.26-7.31 (dd, J=8.3, 5.4 Hz, 2H); 13C (125 MHz, D2O) delta 28.82, 47.1, 53.5, 116.4 (d, J=22 Hz, 2C), 139.7 (d, J=11.6 Hz, 2C), 130.9, 163.2 (d, J=246 Hz, 2C); 19F (282 MHz, D2O) -112.9 to -113.0 (m); ES-MS 232 (M-1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,612532-52-2, 3-Amino-3-(4-fluorophenyl)propan-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; Kong, Xianqi; Wu, Xinfu; Bouzide, Abderrahim; Valade, Isabelle; Migneault, David; Bellini, Francesco; US2006/183800; (2006); A1;,
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