Preparing method of (1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine
A technology of difluorophenyl and cyclopropylamine, which is applied in the field of preparation of -2-cyclopropylamine, can solve the problems of low reaction yield, harsh reaction conditions, and large environmental pollution, and achieve low operating costs, mild preparation process conditions, Avoids the effects of expensive metal catalysts
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Embodiment 1
[0042] Add 150 ml of cyclohexane, 0.75 g of 2-(3,4-difluorophenyl) cyclopropylamine, 0.75 mg of CALB, 0.75 mg of 5% Pd / C, and 0.39 g of acetic acid in a 250 ml Erlenmeyer flask Ethyl ester, put it in a shaker, set the temperature of the shaker at 30°C, 250 rpm, react for 8 hours, take out the Erlenmeyer flask, cool down to 25°C, filter and recover Pd / C, CALB, filtrate rotary evaporation to recover solvent 145 milliliters, dropwise add 16.2 grams of 1% hydrochloric acid aqueous solution in the residual oily matter, stir at 30 ℃ for 8 hours, add dropwise NaOH of 1% mass percent concentration in the solution, control the pH value of the system to be 8-9, add the above 145 milliliters of recovered cyclohexane was extracted, separated into layers, and the organic phase was rotary evaporated to recover cyclohexane to obtain 0.56 g of (1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine, and the chiral gas chromatography column Detection analysis. Gas chromatograph: SHIMADZU GC-2014C; gas...
Embodiment 2
[0046] In a 250 ml Erlenmeyer flask, add 150 ml of n-hexane, 0.75 g of 2-(3,4-difluorophenyl) cyclopropylamine, 7.5 mg of CALB, 7.5 mg of 1% Pd / C, add 1.54 g of tert-acetic acid Put butyl ester in a shaker, set the shaker temperature to 60°C, 250 rpm, react for 24 hours, take out the Erlenmeyer flask, cool down to 25°C, filter and recover Pd / C, CALB, filtrate rotary evaporation to recover n-hexane 140 milliliters of alkane, 16.2 grams of 3% hydrochloric acid aqueous solution was added dropwise to the residual oil, stirred at 70°C for 2 hours, and NaOH of 1% mass percent concentration was added dropwise in the solution to control the pH value of the system to be 8-9, adding 140 ml of n-hexane recovered above was extracted, separated into layers, and the organic phase was rotary evaporated to recover n-hexane to obtain 0.63 g of (1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine, and the measured ee value was 98.8 %.
Embodiment 3
[0048] In a 250 ml Erlenmeyer flask, add 150 ml of toluene, 0.75 g of 2-(3,4-difluorophenyl) cyclopropylamine, 7.5 mg of CALB, 7.5 mg of 3% Pd / C, and 1.89 g of trifluoroacetic acid Acetic acid, put it in a shaker, set the shaker temperature at 60°C, 250 rpm, react for 24 hours, take out the Erlenmeyer flask, cool down to 25°C, filter and recover Pd / C, CALB, filtrate rotary evaporation to recover toluene 145 ml, dropwise add 16.2 grams of 3% hydrochloric acid aqueous solution to the residual oil, stir at 50°C for 2 hours, add dropwise NaOH with 1% mass percent concentration in the solution, control the pH of the system to be 8-9, add the above recovery 140 ml of toluene was extracted, the layers were separated, and the toluene was recovered by rotary evaporation of the organic phase to obtain 0.63 g of (1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine, and the measured ee value was 98.9%.
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