Method for preparing (3S)-3-(4-aminophenyl)-piperidyl-1-tert-butyl formate
A technology of tert-butyl formate and aminophenyl, which is applied in the field of preparation of tert-butyl-3-piperidine-1-carboxylate, can solve the problems of difficult separation of by-products, high cost, and low resolution yield, and achieve the product Yield and improvement, ee value improvement, and the effect of easy availability of raw materials
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Embodiment 1
[0030] A method for preparing (3S)-3-(4-aminophenyl) piperidine-1-carboxylic acid tert-butyl ester, the method comprises the following steps:
[0031] 1) 27.6 g (100 mmol) of tert-butyl 3-(4-aminophenyl) piperidine-1-carboxylate, 38.3 g (110 mmol) of (R)-(-)-binaphthol phosphate, CuI3 .8g (20mmol) was added to 150ml of mixed solvent, the mixed solvent was made up of DMF and water with a volume ratio of 5:1, then was heated to 75°C for contact reaction for 1 hour, after the contact reaction, continued stirring and naturally cooled to 50°C Incubate for 1 hour, then naturally cool to room temperature, and filter to obtain solid compound A.
[0032] 2) The solid compound A obtained in step 1) was hydrolyzed in 50 ml of 10% hydrochloric acid solution. After the hydrolysis reaction was completed, sodium hydroxide was added to adjust the pH of the reaction solution to 10, extracted with ethyl acetate, concentrated, recrystallized from petroleum ether, and vacuumized. Dry to obtain (...
Embodiment 2
[0034] A method for preparing (3S)-3-(4-aminophenyl) piperidine-1-carboxylic acid tert-butyl ester, the method comprises the following steps:
[0035]1) 27.6 g (100 mmol) of tert-butyl 3-(4-aminophenyl) piperidine-1-carboxylate, 41.8 g (120 mmol) of (R)-(-)-binaphthol phosphate, CuI7 .6g (40mmol) is added in 150ml mixed solvent, and described mixed solvent is made up of DMF and water that volume ratio is 7:1, then be warming up to 80 ℃ of contact reactions for 1 hour, after the contact reaction, continue to stir and naturally cool to 45 ℃ Incubate for 1 hour, then naturally cool to room temperature, and filter to obtain solid compound A.
[0036] 2) The solid compound A obtained in step 1) was hydrolyzed in 60 ml of 5% hydrochloric acid solution. After the hydrolysis reaction was completed, sodium hydroxide was added to adjust the pH of the reaction solution to 9, extracted with ethyl acetate, concentrated, recrystallized from petroleum ether, and dried in vacuo 12.5 g of ter...
Embodiment 3
[0038] A method for preparing (3S)-3-(4-aminophenyl) piperidine-1-carboxylic acid tert-butyl ester, the method comprises the following steps:
[0039] 1) 27.6g (10mmol) of tert-butyl 3-(4-aminophenyl)piperidine-1-carboxylate, 36.6g (105mmol) of (R)-(-)-binaphthol phosphate, CuCl2 .8g (30mmol) was added in 180ml mixed solvent, the mixed solvent was made up of DMF and water with a volume ratio of 8:1, then was heated to 85°C for contact reaction for 1.5 hours, after the contact reaction, continued stirring and naturally cooled to 50°C Incubate for 0.5 hours, then naturally cool to room temperature, and filter to obtain solid compound A.
[0040] 2) The solid compound A obtained in step 1) was hydrolyzed in 50 ml of 10% hydrochloric acid solution, and after the hydrolysis reaction was completed, cesium carbonate was added to adjust the pH of the reaction solution to 8, extracted with ethyl acetate, concentrated, recrystallized from petroleum ether, and dried in vacuo to obtain (...
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