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A technology of dutasteride and aniline, which is applied in the field of preparation of chemical drugs, can solve problems such as personal danger of operators, achieve the effects of reducing costs, saving steps, and improving process safety
Inactive Publication Date: 2011-10-19
湖南尔文水电建材有限公司
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Problems solved by technology
Among them, the cyanidation reaction is carried out in an acidic potassium cyanide solution, which easily produces volatile and highly toxic hydrocyanic acid, which brings fatal personal danger to the operator.
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Embodiment 1
[0042] Dissolve 10.0g of androstenedione in 220ml of tert-butanol, add 50ml of an aqueous solution containing 9g of anhydrous potassium carbonate, heat up to 45°C, dropwise add 160ml of an aqueous solution containing 20g of potassium permanganate and 20g of sodium periodate, add Continue the reaction for 0.5 hours, cool to room temperature, filter, remove tert-butanol under reduced pressure, cool, adjust pH to 1-2 with concentrated hydrochloric acid, extract with dichloromethane, dry the organic phase with anhydrous sodium sulfate, and concentrate under reduced pressure A white solid compound 2 was obtained, which was dried to obtain 8.9 g. IR(KBr)(cm -1 ): 3048-3503, 1730, 1706.
Embodiment 2
[0044] 8.5g of compound (2), 26g of ammonium acetate, and 50ml of acetic acid solution were added to a three-necked flask equipped with a reflux condenser, refluxed at 105°C for 3h, cooled, added with 50ml of water, reacted for 12h, filtered, washed with water, and dried in vacuo to obtain compound ( 3) 6.3g. IR(KBr)(cm -1 ): 3185, 3065, 1739, 1675, 1660.
Embodiment 3
[0046] 6 g of compound (3) was dissolved in tetrahydrofuran, and 50 ml of 1.7M methylmagnesium iodide solution in tetrahydrofuran was slowly added dropwise. It was dried over anhydrous sodium sulfate and concentrated to obtain 6.3 g of compound (4). IR(KBr)(cm -1 ) 3429, 3150, 1748, 1683. ESI-MS m / z (%): [M+H] + =303.4; 1H NMR (DMSO) δ: 0.83 (s, 3H, 8-CH 3 ), 0.95(s, 3H, 19-CH 3 ), 1.08(s, 3H, 20-CH 3 ), 3.3 (m, 1H, 5α-H), 7.62 (1H.NH), 8.05 (br.1H.OH).
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Abstract
The invention discloses a method for preparing dutasteride, belonging to the field of chemical synthesis of drugs. In the invention, with androstendione as a raw material, the dutasteride is prepared by eight reaction steps of ring opening, ring closing, Grignard reaction, dehydration, reduction, oxidation, dehydrogenation and condensation. In the method disclosed by the invention, double bonds at sites 5 and 6 and double bonds at sites 16 and 27 are simultaneously hydrogenated and reduced; and amidation of a site 17 and condensation of a site 20 are continuously carried out so that the steps are saved; potassium cyanide under an acidic condition is avoided and the process safety is improved; and the expensive 4-di(trifluoromethyl)-2-iodobenzene is replaced with cheap 2,5-di(trifluoromethyl) aniline so that the cost is largely reduced.
Description
technical field [0001] The invention relates to a preparation method of a chemical drug, in particular to a preparation method of the compound dutasteride. Background technique [0002] Dutasteride (Avodart), chemical name (5alpha, 17beta)-n-{2,5-bis(trifluoromethyl)phenyl}-3-oxo-4-azaandrost-1-ene-17-carboxamide, CAS: 164656-23-9, the structural formula is: [0003] [0004] Dutasteride is a novel dual inhibitor of 5α-reductase, which can inhibit both 5α-reductase 1 and 5α-reductase 2. It has precise curative effect, small dose, and low side effects. Widely acclaimed. [0005] There are many preparation methods of dutasteride, and the preparation method disclosed in WO9507927 includes: the first process route is as follows: [0006] [0007] In this route, pregnenoic acid is used as raw material, and dutasteride is obtained through acylation, ring opening, cyclization, hydrogenation reduction, and dehydrogenation successively. [0008] The second process route is ...
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