Process for preparing guggulsterones and guggulsterol
A technology of diketone and ethanedithiol, which is applied in the direction of steroids, brushes, organic chemistry, etc., can solve the problems such as the yield of the final product myrrhosterone, the danger, and the difficulty of handling acetic acid.
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Embodiment 1
[0191] Embodiment 1: Synthetic ring-3-(1,2-ethylene dithioacetal)-4-androsten-17-ketone of general formula (I-A-1) by the compound of general formula (I-A) [step A ]
[0192] 4-androstene-3,17-dione (I-A) (28.6g, 100mmol) was completely dissolved in glacial acetic acid (100ml) at 25°C, and 1,2-ethanedithiol (10.4ml, 110mmol) and p-Toluenesulfonic acid (8.6 g, 50 mmol) was continuously added to the above solution. The reaction mixture was further reacted at room temperature, and the resulting mixture was poured into distilled water (100 ml), followed by thorough stirring at room temperature for 15 minutes. The resulting mixture was extracted with ethyl acetate (3×50 ml), the organic layer was washed with brine and distilled water, dried over magnesium sulfate, filtered and evaporated under reduced pressure, and the resulting residue was washed with ethyl acetate / hexane (2 / 8) Purified by column chromatography to obtain the title compound (27.2 g, yield: 75%).
[0193] 1 H NM...
Embodiment 2
[0195] Embodiment 2: Synthetic ring-3-(1,2-ethylene dithioacetal)-4-androsten-17-one of general formula (I-A-1) from general formula (I-A) [step A]
[0196] 4-androstene-3,17-dione (I-A) (28.6g, 100mmol) was completely dissolved in anhydrous methanol (150ml) at 0°C, and 1,2-ethanedithiol (15ml, 179mmol) was added The solution was then slowly added to the acidic catalyst BF 3 • Diethyl ether (14ml). The reaction was continued at 20°C for 10 hours. After the reaction was complete, the resulting mixture was evaporated under reduced pressure to remove methanol and washed with dichloromethane (100ml) and 5% NaHCO 3 Solution work up the resulting mixture. The organic layer was dried over magnesium sulfate, filtered and evaporated under reduced pressure to obtain the title compound (33.4 g, yield: 92%).
Embodiment 3
[0197] Embodiment 3: Synthetic ring-3-(1,2-ethylene dithioacetal)-4,17(20)-cis-androstene of general formula (I-A-2) by general formula (I-A-1) [step B]
[0198] Ethyltriphenylphosphonium bromide (44.6g, 120mmol) was dissolved in dry tetrahydrofuran (200ml) at 0°C, 120ml (120mmol). Anhydrous tetrahydrofuran (1 mol solution) dissolved in potassium tert-butoxide was slowly added to the above solution over 15 minutes. After the addition was complete, the reaction mixture was further reacted at room temperature for 30 minutes, and tetrahydrofuran (150 ml) dissolved with a compound of general formula (I-A-1) (33.4 g, 92.1 mmol) was slowly added thereto at room temperature, and the The reaction mixture was stirred at room temperature for 2 hours for further reaction. The resulting mixture was evaporated under reduced pressure, and a mixed solvent of 250ml of hexane and ethyl ester (v / v=10 / 1) was added to generate the by-product triphenylphosphine oxide (Ph 3 P=O) precipitate, whi...
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