A kind of method that iridium catalytic hydrogenation synthesizes 3-piperidone derivatives
A technology of piperidone and hydrogen catalysis, which is applied in the field of synthesizing 3-piperidone derivatives, can solve the problems of long route, cumbersome steps, and difficult scale-up synthesis, and achieve high atom economy, simple reaction operation, and short synthetic route Effect
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Embodiment 1
[0031] Example 1: Optimization of conditions
[0032] In a glove box filled with nitrogen, the solution containing (1,5-cyclooctadiene) iridium chloride dimer (0.001 mmol, 0.7 mg) and phosphine ligand (0.0022 mmol or 0.0044 mmol) Add 1 ml of 1,2-dichloroethane solvent to the reaction flask, stir at room temperature for 10-15 minutes, then transfer the prepared catalyst with a needle tube to another containing raw material 3-hydroxypyridine salt 2a (0.20 mmol, 68.5 Mg) and sodium bicarbonate (0.2 mmol, 16.8 mg) in the reaction flask, wash the bottle with 2 ml of solvent, transfer the remaining catalyst, and share 3 ml of solvent 1,2-dichloroethane. The reaction flask was put into a stainless steel autoclave, and hydrogen gas was injected at 600 psi and reacted at 50°C for 20 hours. Slowly release hydrogen, filter the reaction solution, use a rotary evaporator to remove the solvent and then directly column chromatography (the volume ratio of eluent petroleum ether and ethyl acetat...
Embodiment 2
[0037] Example 2: Synthesis of 3-piperidone derivatives by homogeneous iridium catalytic hydrogenation
[0038] In a glove box filled with nitrogen, (1,5-cyclooctadiene) iridium chloride dimer (0.001 mmol, 0.7 mg) and triphenylphosphine ligand (0.0044 mmol, 1.2 mg) 1 ml of solvent 1,2-dichloroethane was added to the reaction flask of ), stirred at room temperature for 10-15 minutes, and then the prepared catalyst was transferred to another containing raw material 3-hydroxypyridine salt 2 (0.20 mmol ) And sodium bicarbonate (0.2 mmol, 16.8 mg) in a reaction flask, wash the bottle with 2 ml of solvent, transfer the remaining catalyst, and share 3 ml of solvent 1,2-dichloroethane. The reaction flask was put into a stainless steel autoclave, and hydrogen gas was injected at 600 psi and reacted at 50°C for 20-30 hours. Slowly release hydrogen, filter the reaction solution, use a rotary evaporator to remove the solvent and then directly column chromatography (volume ratio of eluent pe...
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