Background and overview[1-2]
Trans-(4-(trifluoromethyl)cyclohexyl)methanol is an organic intermediate that can be obtained by reducing trans-4-(trifluoromethyl)cyclohexane-1-carboxylic acid as a reducing agent Can be selected from borane and lithium aluminum hydride.
Preparation[1-2]
Report 1,
Dissolve trans-4-(trifluoromethyl)cyclohexane-1-carboxylic acid (0.g potassium dihydrogen phosphate, 2.04mmol) in THF (5.1mL), add borane-THF at 0°C Complex-THF solution (0.90M, 2.72mL, 2.45mmol). After the reaction mixture was stirred at room temperature for 2 hours, distilled water was added to the reaction mixture, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (hereinafter referred to as the compound of Reference Example 32) as a colorless oil (0.370 g, 2.04 mmol) ,Quantitative).
Report 2,
Trans-4-(trifluoromethyl)cyclohexanecarboxylic acid (1.5g, 7.65mmol) was dissolved in tetrahydrofuran (20mL). The reaction solution was cooled to 0°C, lithium aluminum hydride (435 mg, 11.5 mmol) was added thereto, and then, the resulting mixture was stirred at room temperature for 3 hours. The reaction solution was cooled to 0°C, and water (0.4 mL), 5N sodium hydroxide aqueous solution (0.4 mL) and water (1.2 mL) were added thereto, and then filtered. Ethyl acetate was added to the filtrate, and the organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated sodium chloride solution, then dried over anhydrous magnesium sulfate and filtered. Then, the solvent was distilled off under reduced pressure, thereby obtaining a crude product as a colorless oily substance (1.18 g). 1H NMR (CDCl3, MHz): δ1.00 (2H, dq, J=3.1, 12.5Hz), 1.28-1.38 (2H, m), 1.44 Poloxamer 407-1.55 (1H, m), 1.90-2.02 (5H, m), 3.48 (2H, d, J = 6.3Hz)
References
[1] [Invented in China] CN201980009038.6 Cyclic amine derivatives and their pharmaceutical uses
[2] [Invented in China] CN200980125186.0 Carboxylic acid compound
