Preparation method of optically pure amino alcohol hydrochloride
A pure aminoalcohol and hydrochloride technology, applied in the field of compound synthesis, can solve the problems of unsatisfactory yield and optical purity of optically pure aminoalcohol products, limited industrial application, environmental protection to be solved, etc., and achieves low production cost and high quality. The effect of stability and less environmental pollution
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Embodiment 1
[0059] Example 1 Preparation of compound 5 and compound 6
[0060] The preparation method of compound 5 and compound 6 of this embodiment comprises the following steps:
[0061] 1) Dissolve 100g (±)-2-azabicyclo[2.2.1]hept-5-en-3-one ((±)-4) in 80ml of methanol, add 110g dropwise at 0°C with stirring After thionyl chloride, continue to stir the reaction mixture at room temperature for 1 h, then add 82.5 g of L-tartaric acid and 50 g of water, and adjust the pH of the reaction solution to 1.8-2 with 60.3 g of triethylamine at 50°C, and then It was cooled to room temperature, continued to stir for 2 hours, vacuum filtered, the filter cake was washed with a small amount of methanol, and dried to obtain 112 g of optically pure compound 5, whose optical purity was ≥ 99% ee;
[0062] 2) Add 123.8g of D-tartaric acid to the filtrate, adjust the pH of the filtrate to 1.5 with 83.5g of triethylamine at 50°C, cool it to room temperature, and continue to stir for 2h; filter under red...
Embodiment 2
[0063] Example 2 Preparation of compound 5 and compound 6
[0064] The preparation method of compound 5 and compound 6 of this embodiment comprises the following steps:
[0065] 1) Dissolve 100g (±)-2-azabicyclo[2.2.1]hept-5-en-3-one ((±)-4) in 80ml methanol, add 110g dropwise at 0°C under stirring After thionyl chloride, continue to stir the reaction mixture at room temperature for 1 h, then add 82.5 g of D-tartaric acid and 50 g of water, and adjust the pH of the reaction solution to 1.8-2 with 60.3 g of triethylamine at 50°C, and then It was cooled to room temperature, continued to stir for 2 hours, vacuum filtered, the filter cake was washed with a small amount of methanol, and dried to obtain 112.1 g of optically pure compound 6, with an optical purity of ≥99% ee;
[0066] 2) Add 123.8g of L-tartaric acid to the filtrate, adjust the pH of the filtrate to 1.5 with 83.5g of triethylamine at 50°C, cool it to room temperature, and continue to stir for 2h; After washing w...
Embodiment 3
[0067] Example 3 Preparation of Optically Pure Amino Alcohol Hydrochloride (1)
[0068] A preparation method of optically pure amino alcohol hydrochloride (1), comprising the steps of:
[0069] 1) Disperse 100g of optically pure compound 5 in 500ml of ethyl acetate, add 75g of triethylamine and 75g of di-tert-butyl dicarbonate (Boc 2 After (0), continue to stir at room temperature for 5 h, and filter off the insoluble matter; the organic layer is washed with water, dried, and spin-dried under reduced pressure to obtain compound 7;
[0070] 2) Dissolve the compound 7 prepared in step 1) in 250ml of tetrahydrofuran, add 20g of sodium borohydride, stir under reflux, add 30ml of methanol dropwise, continue to stir and reflux for 5h, cool to room temperature, quench the reaction with acetic acid, and depressurize The solvent and volatile matter were removed by rotary evaporation, ethyl acetate and water were added, stirred for 30 minutes, and the organic phase was taken; the or...
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