Novel method for synthesizing chiral 4-nitryl-3, 5-diaryl cyclohexanone
A cyclohexanone and chiral technology, applied in the field of asymmetric catalysis, can solve the problems of expensive raw materials and difficult to obtain prices, and achieve the effects of high yield, excellent diastereoselectivity and good enantioselectivity
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[0038] Example one:
[0039]
[0040] Fill the reaction flask with 1a (58.5 mg, 0.25 mmol), nitromethane (263.2 uL, 5.0 mmol) and thiourea catalyst (29.7 mg, 0.05 mmol), add 1mL of toluene, and react at room temperature for 24-72 hours. Column chromatography (eluent: ethyl acetate: petroleum ether=1:5-1:10) After separating the raw materials and the catalyst, the residue is dissolved in potassium hydroxide (1.1 mg, 0.020 mmol) in ethanol (2 mL) In, react at 0°C for 2 hours to obtain a crude product;
[0041] The reaction system was quenched with saturated ammonium chloride, extracted with ethyl acetate, the organic layer was dried with anhydrous sodium sulfate, the solvent was removed, and the crude product was passed through simple column chromatography (eluent: ethyl acetate: petroleum ether = 1:10 ) The target product 3a (63.5mg) can be obtained with a yield of 86%.
[0042] The product is analyzed, and the results are as follows: 1 H NMR (400 MHz, CDCl 3 ): δ 7.34 – 7.27 (m, 2H...
Example Embodiment
[0043] Embodiment two:
[0044]
[0045] Fill the reaction flask with 1a (58.5 mg, 0.25 mmol), nitromethane (263.2 uL, 5.0 mmol) and thiourea catalyst (29.7 mg, 0.05 mmol), add 1mL of toluene, and react at room temperature for 24-72 hours. Column chromatography (eluent: ethyl acetate: petroleum ether=1:5-1:10) After separating the raw materials and the catalyst, the residue is dissolved in potassium hydroxide (1.1 mg, 0.020 mmol) in ethanol (2 mL) In, react at 0°C for 2 hours to obtain a crude product;
[0046] The reaction system was quenched with saturated ammonium chloride, extracted with ethyl acetate, the organic layer was dried with anhydrous sodium sulfate, the solvent was removed, and the crude product was passed through simple column chromatography (eluent: ethyl acetate: petroleum ether = 1:10 ) The target product 3a' (28.1mg) can be obtained with a yield of 38%.
[0047] The product is analyzed, and the results are as follows: 1 H NMR (400 MHz, CDCl 3 ): δ 7.34 – 7.27 (m...
Example Embodiment
[0048] Embodiment three:
[0049]
[0050] Fill the reaction flask with 1b (88.5 mg, 0.25 mmol), nitromethane (263.2 uL, 5.0 mmol) and thiourea catalyst (29.7 mg, 0.05 mmol), add 1mL of toluene, and react at room temperature for 24-72 hours. Column chromatography (eluent: ethyl acetate: petroleum ether=1:5-1:10) After separating the raw materials and the catalyst, the residue is dissolved in potassium hydroxide (1.1 mg, 0.020 mmol) in ethanol (2 mL) In, react at 0°C for 2 hours to obtain a crude product;
[0051] The reaction system was quenched with saturated ammonium chloride, extracted with ethyl acetate, the organic layer was dried with anhydrous sodium sulfate, the solvent was removed, and the crude product was passed through simple column chromatography (eluent: ethyl acetate: petroleum ether = 1:10 ) The target product 3b (79.8mg) can be obtained with a yield of 77%.
[0052] The product is analyzed, and the results are as follows: 1 H NMR (300 MHz, CDCl 3 ): δ 6.37 (s, 3H),...
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