Synthetic method of abiraterone acetic ester
A technology for the synthesis of abiraterone acetate and its application in the fields of steroids and organic chemistry, which can solve the problems of long Suzuki coupling reaction time and achieve the effects of industrial production, high overall yield and easy operation
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Embodiment 1
[0023] Add 3.3 g (10 mmol) of dehydroepiandrosterone acetate, 2.5 g (12 mmol) of aluminum isopropoxide, 10 mL of isopropanol, and 10 mL of toluene into a 250 mL three-neck flask, and carry out the reduction reaction at 130 ° C for 10 hours. Properly cool and add 6g of molecular sieve (as desiccant and decolorizer at the same time), heat and reflux for dehydration, then add 1.6g (11 mmol) of 3-bromopyridine, 0.3g (1.1 mmol) of palladium acetate, 1.1g (1.1 mmol) of triethylamine after cooling , heated to reflux for 15 hours, concentrated, column chromatography cyclohexane:ethyl acetate (volume ratio) = 5:2 mixed solvent as a developing solvent for separation and purification, to obtain 2.34g of product, yield 60%.
[0024] Melting point 128~130℃. 1H NMR (400 MHz, CDCl3) δ: 1.05 (s, 3H, 19-CH3), 1.08 (s, 3H, 18-CH3), 2.04 (s, 3H, CH3CO2), 3.51 ~ 3.58 (m, 1H, 3α -H), 5.39 (d, J=4.7 Hz, 1H, 6-H), 6.00 (s, 1H, 16-H), 7.22 (dd, J1=4.8 Hz, J2=7.8 Hz, 1H, Py 5- H), 7.66 (d, J=7.9 Hz,...
Embodiment 2
[0026] Add 3.3 g (10 mmol) of dehydroepiandrosterone acetate, 2.5 g (12 mmol) of aluminum isopropoxide, 10 mL of isopropanol, and 50 mL of toluene into a 250 mL three-neck flask, and carry out the reduction reaction at 50 ° C for 15 hours. Properly cool and add 1g of molecular sieve, 2g of activated carbon (as desiccant and decolorizer at the same time), heat and reflux for dehydration, then add 1.6g (11 mmol) of 3-bromopyridine, 0.3g (1.1 mmol) of palladium acetate, 1.1g of triethylamine ( 1.1 mmol), heated to reflux for 15 hours, concentrated, column chromatography cyclohexane: ethyl acetate (volume ratio) = 5:2 mixed solvent was used as a developing solvent for separation and purification to obtain 2.34 g of the product, with a yield of 60%.
Embodiment 3
[0028] Add 3.3 g (10 mmol) of dehydroepiandrosterone acetate, 2.5 g (12 mmol) of aluminum isopropoxide, 5 mL of isopropanol, and 50 mL of toluene into a 250 mL three-necked flask, and carry out the reduction reaction at 150 ° C for 5 hours, and After cooling, add 3g of molecular sieve, 9g of diatomaceous earth (both as desiccant and decolorizing agent), heat and reflux for dehydration, then add 1.6g (11 mmol) of 3-bromopyridine, 0.3g (1.1 mmol) of palladium acetate, and 1.1g of triethylamine (1.1 mmol), heated to reflux for 15 hours, concentrated, column chromatography cyclohexane: ethyl acetate (volume ratio) = 5:2 mixed solvent as a developing solvent for separation and purification, the product was 2.4g, yield 61%.
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