Optically active indole derivative, synthetic method and application thereof
A technology of indole derivatives and optical activity, applied in the direction of organic active ingredients, chemical instruments and methods, drug combinations, etc., to achieve the effect of simple and safe operation, high yield, and efficient construction
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Embodiment 1
[0043] (2-1)
[0044] N-methylindole (0.3 mmol), Rh 2 (OAc) 4 (0.0025 mmol), the chiral small molecule catalyst PPA (0.005 mmol) and 4? molecular sieves (0.1 g) were dissolved in toluene (1 ml), and then, the (0.25mmol,) was added dropwise in the reaction system within 1 hour, and the reaction system was at 0°C. After the dropwise addition was completed, it was stirred for 1 hour, and the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product, which had a structure such as formula (2 -1) as shown. The crude product was subjected to column chromatography (ethyl acetate:petroleum ether=1:100~1:40) to obtain a pure product. The yield was 96%, ee%=92%. nuclear magnetic resonance 1 H NMR, 13 C NMR spectrum as figure 1Shown, product 4a 1H NMR (400MHz, CDCl3) δ (ppm) 3.69 (s, 3H), 3.72 (s, 3H), 5.25 (s, 1H), 7.02-7.07 (m, 2H), 7.17-7.31 ( m, 5H), 7.40-7.45 (m, 3H); 13C NMR (400Hz, CDCl3) δ (ppm) 32.80, 48.87, 52.32, 109.40, 112.14, 119.09...
Embodiment 2
[0046] (2-2)
[0047] N-methylindole (0.3 mmol), (0.3 mmol), Rh 2 (OAc) 4 (0.0025 mmol), the chiral small molecule catalyst PPA (0.005 mmol) and 4? molecular sieves (0.1 g) were dissolved in toluene (1 ml), and then the p-methoxyphenyl Nitroacetic acid methyl ester (0.25mmol,) was added dropwise to the reaction system within 1 hour, and the reaction system was at 0°C. After the dropwise addition was completed, it was stirred for 1 hour, and the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product with the structure As shown in formula (2-2). The crude product was subjected to column chromatography (ethyl acetate:petroleum ether=1:100~1:40) to obtain a pure product. The yield was 93%, ee%=89%. nuclear magnetic resonance 1 H NMR, 13 C NMR spectrum as figure 2 As shown, product 4b 1H NMR (400MHz, CDCl3) δ (ppm) 3.69 (s, 3H), 3.71 (s, 3H), 3.73 (s, 3H), 5.19 (s, 1H), 6.81-6.84 (m, 2H), 7.00-7.06 (m, 2H), 7.18 (t, J=7.2Hz, 1H), 7.19-...
Embodiment 3
[0049] (2-3)
[0050] N-methylindole (0.3 mmol), Rh 2 (OAc) 4 (0.0025 mmol), chiral small molecule catalyst PPA (0.005 mmol) and 4? molecular sieves (0.1 g) were dissolved in toluene (1 ml), then, 4-bromophenyldiazo Methyl acetate (0.25mmol,) was added dropwise in the reaction system within 1 hour, and the reaction system was at 0°C. After the dropwise addition was completed, it was stirred for 1 hour, and the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product whose structure was as follows: Formula (2-3) shows. The crude product was subjected to column chromatography (ethyl acetate:petroleum ether=1:100~1:40) to obtain a pure product. The yield was 95%, ee%=90%. nuclear magnetic resonance 1 H NMR, 13 C NMR spectrum as image 3 Shown, product 4c 1H NMR (400MHz, CDCl3) δ (ppm) 3.80 (s, 3H), 3.81 (s, 3H), 5.28 (s, 1H), 7.11-7.15 (m, 2H), 7.27-7.29 ( m, 1H), 7.34-7.37 (m, 3H), 7.46-7.50 (m, 3H); 13C NMR (400Hz, CDCl3) δ (ppm) 32.8...
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