Extracurricular laboratory: Synthetic route of 1202577-61-4

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1202577-61-4, trans-(4-(Trifluoromethyl)cyclohexyl)methanol, and friends who are interested can also refer to it.

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1202577-61-4, name is trans-(4-(Trifluoromethyl)cyclohexyl)methanol, molecular formula is C8H13F3O, molecular weight is 182.18, as common compound, the synthetic route is as follows.Recommanded Product: 1202577-61-4

(45B) Methyl (3S)-3-ethoxy-3-(4-{[trans-4-(trifluoromethyl)cyclohexyl]methoxy}phenyl)propionateMethyl (3S)-3-ethoxy-3-(4-hydroxyphenyl)propionate (150 mg, 0.669 mmol) produced in Example 41 (41C) and [trans-4-(trifluoromethyl)cyclohexyl]methanol (183 mg, 1.00 mmol) produced in (45A) were dissolved in tetrahydrofuran (5 mL), and triphenylphosphine (350 mg, 1.34 mmol) and a 40% diethyl azodicarboxylate toluene solution (600 muL, 1.34 mmol) were added thereto at room temperature, and then, the resulting mixture was stirred under a nitrogen atmosphere at 50 C. for 3 hours.After the reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 80:20 (v/v)), whereby the objective title compound was obtained as a colorless oily substance (103 mg, yield: 40%).1H NMR (CDCl3, 400 MHz): delta1.07-1.17 (2H, m), 1.14 (3H, t, J=7.0 Hz), 1.30-1.43 (2H, m), 1.74-1.86 (1H, m), 1.95-2.05 (5H, m), 2.56 (1H, dd, J=5.1, 15.3 Hz), 2.81 (1H, dd, J=9.0, 15.3 Hz), 3.30-3.39 (2H, m), 3.67 (3H, s), 3.77 (2H, d, J=6.3 Hz), 4.68 (1H, dd, J=5.1, 9.0 Hz), 6.86 (2H, d, J=9.0 Hz), 7.25 (2H, d, J=9.0 Hz)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1202577-61-4, trans-(4-(Trifluoromethyl)cyclohexyl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; DAIICHI SANKYO COMPANY, LIMITED; US2011/53974; (2011); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts