A kind of preparation method of chiral trifluoromethyl allylamine compound
A technology of trifluoromethylallylamine and trifluoromethylallyl sulfinamide, which is used in the preparation of pharmaceuticals, chemical intermediates, the preparation of chiral trifluoromethylallylamine compounds, and pesticides. It can solve the problems of low yield and complex process of trifluoromethylallylamine compounds, and achieve the effects of short reaction time, significant technological progress and good application prospects.
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Embodiment 1
[0029] Under nitrogen protection, add 2 mL of anhydrous tetrahydrofuran and unsaturated imine to the reaction tube (62.3mg, 0.2mmol), CsF (34mg, 0.22mmol) was cooled to 0°C, TMSCF was added 3 Reagent (143.2mg, 1mmol), after the completion, the reaction was incubated, stirred, and TLC followed the reaction until it was complete. Add 5 ml of saturated aqueous ammonium chloride solution. The liquid was separated, extracted with ethyl acetate, and dried over anhydrous sodium sulfate. The solvent was removed by rotary evaporation, and the product was obtained by flash column chromatography 74.7 mg, yield 98%.
[0030] 1 H NMR (400MHz, CDCl 3 ):δ7.21-7.86(m,10H),7.04(d,J=16.2Hz,1H),6.63(d,J=16.2Hz,1H),4.12(s,1H),1.28(s,9H) ; 19 F NMR (376MHz, CDCl 3 ):δ-73.59(s,3F); 13 C NMR (101MHz, CDCl 3 ): δ135.63, 135.32, 133.93, 129.38, 129.35, 128.71, 128.60, 128.41, 127.01, 125.98, 125.39 (q, J = 286.6 Hz), 69.13 (q, J = 27.0 Hz), 57.27, 22.68.
Embodiment 2
[0032] Under nitrogen protection, add 2 mL of anhydrous tetrahydrofuran and unsaturated ketimine to the reaction tube (68.3mg, 0.2mmol), CsF (34mg, 0.22mmol) was cooled to 0°C, TMSCF was added 3 Reagent (143.2mg, 1mmol), after the completion, the reaction was incubated, stirred, and TLC followed the reaction until it was complete. Add 5 ml of saturated aqueous ammonium chloride solution. The liquid was separated, extracted with ethyl acetate, and dried over anhydrous sodium sulfate. The solvent was removed by rotary evaporation, and the product was obtained by flash column chromatography 41.2 mg, 50% yield.
[0033] 1 H NMR (400MHz, CDCl 3 ):δ7.22-7.59(m,7H),7.05(d,J=16.3Hz,1H),6.92(d,J=8.9Hz,2H),6.61(d,J=16.3Hz,1H),4.09 (s,1H),3.82(s,3H),1.27(s,9H); 19 F NMR (376MHz, CDCl 3 ):δ-73.99(s,3F); 13 C NMR (101MHz, CDCl 3 ), 57.13, 55.26, 22.74.
Embodiment 3
[0035] Under nitrogen protection, add 2 mL of anhydrous tetrahydrofuran and unsaturated ketimine to the reaction tube (69.2mg, 0.2mmol), CsF (34mg, 0.22mmol) was cooled to 0°C, TMSCF was added 3 Reagent (143.2mg, 1mmol), after the completion, the reaction was incubated, stirred, and TLC followed the reaction until it was complete. Add 5 ml of saturated aqueous ammonium chloride solution. The liquid was separated, extracted with ethyl acetate, and dried over anhydrous sodium sulfate. The solvent was removed by rotary evaporation, and the product was obtained by flash column chromatography 66.5 mg, 80% yield.
[0036] 1 H NMR (400MHz, CDCl 3 ):δ7.25-7.70(m,9H),7.02(d,J=16.3Hz,1H),6.59(d,J=16.3Hz,1H),4.11(s,1H),1.28(s,9H) ; 19 F NMR (376MHz, CDCl 3 ):δ-73.80(s,3F); 13 C NMR (101MHz, CDCl 3 ), 57.37, 22.69.
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