Synthesis of alpha-hydroxyl-beta-aminophenol with optical activity
A technology of optical activity and synthetic method, which is applied in organic chemical methods, chemical instruments and methods, organic chemistry, etc., can solve the problems of cumbersome operation, high cost, and low yield, and achieve simple and safe operation, high selectivity, high Yield effect
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[0036] Example 1
[0037] Dissolve p-anisidine (0.25mmol), benzaldehyde (0.3mmol), chiral phosphoric acid catalyst A (Ar=9-phenanthryl) (0.005mmol) as shown in the structural formula on the right in CH 2 Cl 2 (1.5ml), then add MgSO 4 (0.1g) and Molecular sieve (0.1g) constituted the reaction system, stirred at room temperature for 12 hours, after which the Rh 2 (OAc) 4 (0.005mmol), anthryl methanol (0.25mmol) was added to the reaction system, cooled to -20°C, and p-methoxyphenyl methyl diazoacetate (0.275mmol) was dissolved in 1mL CH 2 Cl 2 To form a solution, use an automatic injection pump to dissolve p-methoxyphenyl methyl diazoacetate in CH 2 Cl 2 The solution was added dropwise to the reaction system within 1 hour. After sample injection, stir at -20°C for 3 hours, and then add saturated NaHCO dropwise to the reaction system 3 Aqueous solution (0.1ml) was used to quench the reaction. The solvent was removed by rotary evaporation under reduced pressure to obtain a crude produ...
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[0039] Example 2
[0040] P-methoxyaniline (0.25mmol), p-bromobenzaldehyde (0.3mmol), and the same chiral phosphoric acid A as in Example 1: Ar=9-phenanthryl (0.005mmol) were dissolved in chloroform (1.5ml) ), then add solid MgSO 4 (0.1g) and A molecular sieve (0.1g) formed a reaction system, stirred at room temperature for 12 hours, then Cu(OTf) (0.005mmol) and anthrylmethanol (0.25mmol) were added to the reaction system and cooled to 20°C. Methyl p-methoxyphenyl diazoacetate (0.275 mmol) was dissolved in 1 mL of chloroform to form a solution, and this solution was added dropwise to the reaction system within 1 hour using an automatic injection pump. After sample injection, stir at 20°C for 3 hours, and then add saturated NaHCO dropwise to the reaction system 3Aqueous solution (0.1ml) was used to quench the reaction. The solvent was removed by rotary evaporation under reduced pressure to obtain a crude product. The crude product is subjected to column chromatography (ethyl aceta...
Example Embodiment
[0041] Example 3
[0042] Dissolve p-anisidine (0.25mmol), o-bromobenzaldehyde (0.3mmol), and the same chiral phosphoric acid A as in Example 1: Ar=9-phenanthryl (0.005mmol) in toluene (1.5ml), Add solid MgSO 4 (0.1g) and Molecular sieve (0.1g) formed a reaction system, stirred at room temperature for 12 hours, and then Rh 2 (OAc) 4 (0.005mmol), anthrylmethanol (0.25mmol) was added to the reaction system and cooled to 10°C. Methyl p-methoxyphenyl diazoacetate (0.275 mmol) was dissolved in 1 mL of toluene, and this solution was added dropwise to the reaction system within 1 hour using an automatic injection pump. After sample injection, stir at 10°C for 3 hours, then add saturated NaHCO dropwise to the reaction system 3 Aqueous solution (0.1ml) was used to quench the reaction. The solvent was removed by rotary evaporation under reduced pressure to obtain a crude product. The crude product is subjected to column chromatography (ethyl acetate: petroleum ether = 1:50 to 1:20) to obta...
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