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cis-N-{2-methoxy-5-[5-(trifluoromethyl)-1H-tetrazol-1-yl]benzyl}-3-phenylpiperidin-4-amine dihydrochloride[ No CAS ]
[ 97628-91-6 ]
cis-1-[(1-acetyl-3-azetidinyl)carbonyl]-N-{2-methoxy-5-[5-(trifluoromethyl)-1H-tetrazol-1-yl]benzyl}-3-phenyl-4-piperidinamine hydrochloride[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
40%
General procedure: To a mixture of 32 (0.15 g, 0.30 mmol), acetic acid (0.022 g, 0.36 mmol), HOBt (0.055 g, 0.36 mmol) and Et3N (0.061 g, 0.60 mmol) in DMF (3 mL) was added WSC (0.069 g, 0.36 mmol). After stirring at room temperature for 14 h, the reaction mixture was poured into H2O and extracted with EtOAc. The extract was washed with aqueous NaHCO3 and brine, dried and concentrated. The residue was purified by preparative HPLC to give an oil, which was treated with 1 equiv of 4 N HCl-EtOAc to provide 36 (0.12 g, 78%)
With oxalyl dichloride; In dichloromethane; water; at 0 - 20℃; for 1.5h;
1-Acetylazetidine-3-carboxylic acid 11a (1500 mg, 10.48 mmol) was dissolved in 20 mL of dichloromethane, and cooled to 0C. The above solution was then added with oxalyl chloride (1995.2 mg, 15.72 mmol), and reacted at room temperature for 1.5 hours. The reaction solution was concentrated under reduced pressure to remove the organic solvent to give the crude title product 11b (1600 mg, yellow solid), which was used directly in the next step without purification.
With palladium 10% on activated carbon; hydrogen; In ethanol; at 40℃; under 15001.5 Torr; for 24.0h;
General procedure: At room temperature, in a three-necked flask, 95.3 g of 1-benzylazetidin-3-carbaldehyde in step (1), a tetrahydrofuran solution, and purified water were sequentially added, and mechanical stirring was started.Reduce the temperature to 0 C and slowly add 37.7 g of sodium chlorite.The temperature was raised to 20-30 C for 15-20 hours. After the reaction was completed, ethyl acetate was added for extraction.After extraction and concentration under reduced pressure, the intermediate 1-benzylazetidine-3-carboxylic acid was obtained.Add 1-benzylazetidin-3-carboxylic acid, ethanol,10% palladium carbon, heated to 40 C, hydrogen gas was passed in, and the pressure was controlled at 2 MPa for 24 hours.After the reaction, the palladium carbon was filtered, and the ethanol was concentrated under reduced pressure to obtain a crude azetidine-3-carboxylic acid.Recrystallized from ethyl acetate, filtered, the filter cake was rinsed with ethyl acetate, dried,35.3 g of pure azetidine-3-carboxylic acid was obtained,The yield was 82.8%, and the GC purity was 99.2%.
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