N-N axial chiral pyrrole amide tertiary amine catalyst as well as preparation method and application thereof
A technology of pyrrole amide and tertiary amine catalyst, which is applied in the directions of catalytic reactions, organic chemistry methods, chemical instruments and methods, etc., can solve the problems of poor stereoselectivity control, poor catalytic effect, etc., and is suitable for industrialized large-scale production, catalytic Excellent effect, good stereoselectivity effect
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Embodiment 1
[0025] The synthetic route of the present embodiment is as follows:
[0026]
[0027] Compound 1 (167 mg, 0.43 mmol), potassium hydroxide (482 mg, 8.6 mmol) were added to 3 mL of methanol, then 1 mL of water was added, and the reaction was stirred at 60° C. The reaction was followed by TLC to the end, and 6N hydrochloric acid solution was used to adjust the pH to 1, extracted with dichloromethane, dried over anhydrous sodium sulfate, and then concentrated to obtain compound 3 (150 mg, 97% yield).
[0028] The structural characterization data of product 3 are as follows:
[0029] m.p.141.9-143.0°C; [α] D 20 =-42.9(c 0.70, Acetone); 1 H NMR (400MHz, DMSO-d 6 ): δ7.78(d,J=8.0Hz,1H),7.44(s,1H),7.38-7.32(m,1H),7.26-7.20(m,1H),7.12-7.08(m,3H), 6.99–6.94(m, 2H), 6.89(d, J=8.3Hz, 1H), 6.79(s, 1H), 2.00(s, 3H); 13 C NMR (100MHz, DMSO-d 6 ): δ166.1, 160.9, 138.8, 138.1, 133.2, 130.5, 129.0, 128.9, 127.9, 127.7, 126.5, 123.7, 123.5, 123.0, 111.9, 111.1, 109.7, 108.1, 10.1; ,15...
Embodiment 2
[0031] The synthetic route of the present embodiment is as follows:
[0032]
[0033] Compound 3 (72.0 mg, 0.2 mmol), 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI) (115 mg, 0.6 mmol), 1-hydroxybenzotriazole (HOBT) (81.0 mg, 0.6 mmol) was added to 2 mL of dichloromethane, and compound 2a (70.4 mg, 0.8 mmol) and triethylamine (NEt 3 ) (60.7 mg, 0.6 mmol), the reaction was stirred at 25 ° C, and the reaction was followed by TLC to the end; the reaction solution was extracted with dichloromethane, then the organic phase was adjusted to pH 1 with 2N hydrochloric acid solution, the organic phase was discarded, and the aqueous phase was saturated with The sodium carbonate solution was adjusted to pH 9-10, extracted with dichloromethane, dried, concentrated, and purified by column chromatography to obtain compound 4a (57.2 mg, 57% yield).
[0034] The structural characterization data of product 4a are as follows:
[0035] m.p.67.4-68.2°C; [α] D 20 =-24.0(c 0...
Embodiment 3
[0037] The synthetic route of the present embodiment is as follows:
[0038]
[0039] Compound 3 (36.0 mg, 0.1 mmol), EDCI (47.9 mg, 0.25 mmol), HOBT (29.7 mg, 0.22 mmol) were added to 1 mL of dichloromethane, and compound 2b (42.7 mg, 0.3 mmol) and NEt were added under stirring 3 (30.4mg, 0.3mmol), the reaction was stirred at 25°C, the reaction was followed by TLC to the end, the reaction solution was extracted with dichloromethane, the organic phase was then adjusted to pH 1 with 2N hydrochloric acid solution, the organic phase was discarded, and the aqueous phase was used saturated carbonic acid The sodium solution was adjusted to pH 9-10, extracted with dichloromethane, dried, concentrated, and purified by column chromatography to obtain compound 4a (46.7 mg, 77% yield).
[0040] The structural characterization data of product 4b are as follows:
[0041] m.p.108.7-109.6℃; >95:5dr; 1 H NMR (400MHz, CDCl 3 ): δ7.66(d,J=7.9Hz,1H),7.33-7.27(m,1H),7.23-7.18(m,2H),7.10-7.0...
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