4-tert-butoxycarbonyl-hexahydro-2H-furo [3,2-b] pyrrole-6-carboxylic acid synthetic method
A technology of tert-butoxycarbonyl and synthesis method, which is applied in the field of synthesis of 4-tert-butoxycarbonyl-hexahydro-2H-furo[3,2-b]pyrrole-6-carboxylic acid, can solve the problem of unsuitable industrialization Synthetic methods and other issues, to achieve the effect of convenient operation, easy reaction, and short route
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Embodiment 1
[0010] Example 1: Compound 1 (8.0g, 0.0310mol) was dissolved in tetrahydrofuran (60mL), cooled to -20 degrees Celsius, and potassium tert-butoxide (8.7g, 0.0777mol) was added, stirred for half an hour, and then added dropwise under nitrogen protection After the addition of bromochloroethane (6.5 g, 0.0451 mol), the temperature of the reaction was raised to 15 degrees Celsius overnight. TLC (petroleum ether: ethyl acetate volume ratio=5 / 1, R f =0.5) showed that the reaction was complete, the reaction mixture was quenched with saturated ammonium chloride solution (30 mL), and extracted with ethyl acetate (20 mLx3). The organic phase was dried with anhydrous sodium sulfate and concentrated, the residue was purified by column chromatography, the eluent ratio was (petroleum ether: ethyl acetate volume ratio = 20 / 1), and compound 2 in yellow oil was obtained after removing the solvent (9.9 g), yield 100%.
[0011] Compound 2 (9.9 g, 0.0310 mol) was dissolved in tetrahydrofuran (80...
Embodiment 2
[0017] Example 2: Dissolve compound 1 (80g, 0.310mol) in tetrahydrofuran (600mL), cool to -20 degrees Celsius, add potassium tert-butoxide (87g, 0.777mol), stir for half an hour, then add bromochloride dropwise under nitrogen protection Ethane (65 g, 0.451 mol), after the addition was complete, the reaction was warmed to 15°C overnight. TLC (petroleum ether: ethyl acetate volume ratio=5 / 1, R f =0.5) showed that the reaction was complete, the reaction mixture was quenched with saturated ammonium chloride solution (300mL), and extracted with ethyl acetate (200mLx3). The organic phase was dried with anhydrous sodium sulfate and concentrated, the residue was purified by column chromatography, the eluent ratio was (petroleum ether: ethyl acetate volume ratio = 20 / 1), and compound 2 in yellow oil was obtained after removing the solvent (95g), yield 96%.
[0018] Compound 2 (95g, 0.298mol) was dissolved in tetrahydrofuran (800mL), sodium hydrogen (12.4g, 0.31mol) was added under ni...
Embodiment 3
[0024] Example 3: Dissolve compound 1 (300 g, 1.18 mol) in tetrahydrofuran (3.0 L), cool to -20 degrees Celsius, add potassium tert-butoxide (330 g, 2.95 mol), stir for half an hour, then add bromine dropwise under nitrogen protection Ethyl chloride (253g, 1.77mol), after the addition was complete, the reaction was warmed to 15°C overnight. TLC (petroleum ether: ethyl acetate volume ratio=5 / 1, R f =0.5) showed that the reaction was complete, the reaction mixture was quenched with saturated ammonium chloride solution (1.0L), and extracted with ethyl acetate (1.0Lx3). The organic phase was dried with anhydrous sodium sulfate and then concentrated, and the residue was purified by column chromatography, the eluent ratio was (petroleum ether: ethyl acetate volume ratio = 20 / 1), and compound 2 in yellow oil was obtained after removing the solvent (372g), yield 98.8%.
[0025] Compound 2 (372g, 1.18mol) was dissolved in tetrahydrofuran (3.0L), sodium hydrogen (70g, 1.77mol) was add...
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