Preparation method and application of (2r,3s,4s)-4-amino-2-tetradecylpyrrolidin-3-ol
A tetradecylpyrrolidine and pyrrolidine technology, which can be used in organic chemistry, antitumor drugs, drug combinations, etc., can solve the problems of long reaction time, complicated operation, low reproducibility, etc., and achieve high reproducibility, Simple operation and mild reaction conditions
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Embodiment 1
[0042] The synthesis of embodiment 1 intermediate compound 2
[0043] Compound 1 (1.08g, 2.4mmol) was dissolved in dichloromethane (9.6mL), pyridine (396μL, 4.8mmol) was added, and trifluoromethanesulfonic anhydride (605μL, 3.6 mmol), reacted for 20 min, and detected the disappearance of the starting point by TLC (ethyl acetate-petroleum ether=1:2). The reaction solution was diluted with dichloromethane, washed successively with 1M hydrochloric acid at 0°C, saturated sodium bicarbonate at 0°C, ice water, and saturated brine at 0°C, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure, and the obtained crude product was directly Dissolved in benzylamine (7.2mL), reacted at 35°C for 1h under nitrogen protection, and the reaction solution was separated and purified by silica gel column chromatography (ethyl acetate-dichloromethane-petroleum ether=3:3:4) to obtain the compound 2 (0.787 g, 61%). 1 H NMR (CDCl 3 ,600MHz)δ(ppm):7.94(...
Embodiment 2
[0044] The synthesis of embodiment 2 intermediate compound 2
[0045] Compound 1 (0.36g, 0.8mmol) was dissolved in dichloromethane (5.0mL), pyridine (132μL, 1.6mmol) was added, and trifluoromethanesulfonic anhydride (202μL, 1.2mmol), reacted for 20min, and detected the disappearance of raw material spots by TLC (ethyl acetate-petroleum ether=1:2). The reaction solution was diluted with dichloromethane, washed successively with 1M hydrochloric acid at 0°C, saturated sodium bicarbonate at 0°C, ice water, and saturated brine at 0°C, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure to obtain the crude product It was directly dissolved in benzylamine (3.0 mL), reacted at 35°C for 1 h under the protection of nitrogen, and the reaction solution was separated and purified by silica gel column chromatography (ethyl acetate-dichloromethane-petroleum ether=3:3:4) to obtain Compound 2 (0.335 g, 78%).
Embodiment 3
[0046] The synthesis of embodiment 3 intermediate compound 2
[0047] Compound 1 (1.44g, 3.2mmol) was dissolved in dichloromethane (20.0ml), pyridine (528μL, 6.4mmol) was added, and trifluoromethanesulfonic anhydride (808μL, 4.8 mmol), reacted for 20 min, and detected the disappearance of the starting material point by TLC (ethyl acetate-petroleum ether=1:2). The reaction solution was diluted with dichloromethane, washed successively with 1 M hydrochloric acid at 0°C, saturated sodium bicarbonate at 0°C, ice water, and saturated brine at 0°C, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure to obtain the crude product It was directly dissolved in benzylamine (12.0 mL), reacted at 35°C for 1 h under the protection of nitrogen, and the reaction solution was separated and purified by silica gel column chromatography (ethyl acetate-dichloromethane-petroleum ether=3:3:4) to obtain Compound 2 (1.308 g, 76%).
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