Chiral phase transfer catalyst and synthesizing method thereof
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A synthesis method and catalyst technology, applied in the field of synthesis of new chiral phase transfer catalysts, can solve problems such as insufficient scope of application, difficult application, complex synthesis, etc.
Inactive Publication Date: 2012-08-08
YANGZHOU TIANHE PHARM CO LTD
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[0005] Although the asymmetric phase transfer catalytic reaction has many advantages, there are still some problems in its development at present. For example, the catalyst of Maruoka has a good catalytic effect, but its structure is relatively complicated, and the synthesis is also relatively complicated, so it is difficult to
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example 1
[0019] In a reaction flask, add 0.391g (1.3mmol) of cinchonaline, dissolve it with 10ml of dimethylformamide (DMF), then add 0.518g (13mmol) of NaH, react for 2 hours, and then drop in dibromoethane 0.26 g (1.43mmol), reacted at room temperature for 2 hours, and raised the temperature to 60°C for 2 hours. After the reaction, added water, extracted with ethyl acetate, separated the organic layer, dried, and spun off the solvent to obtain the catalyst.
example 2
[0021] In a reaction flask, add 0.391g (1.3mmol) of cinchonaline, dissolve it with 10ml of tetrahydrofuran (THF), then add 0.518g (13mmol) of NaH, react for 2 hours, then drop into 0.26g (1.43mmol) of dibromoethane ), react at room temperature for 2 hours, and raise the temperature to 60°C for 2 hours. After the reaction, add water, extract with ethyl acetate, separate the organic layer, dry, and spin off the solvent to obtain the catalyst.
[0022] 2. Application: for asymmetric alkylation of glycine tert-butyl ester derivatives
[0023] example 1:
[0024] In the reaction bottle, add 5.68 mg of the prepared catalyst, dissolve it in 2 ml of toluene, add 0.1 g of 50% potassium hydroxide, stir for 1 hour, and add 29.6 mg of glycine tert-butyl ester derivative ( 2-Dibenzyl iminoacetate tert-butyl), and react at this temperature for 1 hour, then add 12 μL of alkylating reagent, and keep the temperature at 0 ℃ for reaction, after the reaction is completed, add water, and dichloro...
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Abstract
The invention discloses a chiral phase transfer catalyst and a synthesizing method thereof, which relate to chemical synthesis and in particular relates to the technical field of synthesis of the novel chiral phase transfer catalyst. The method comprises the following steps of dissolving quinine in solvent, reacting with sodium hydride, reacting by adding hydrocarbon dihalide, extracting to obtain an organic layer, drying, and re-separating for removing the solvent so as to obtain the chiral phase transfer catalyst. The chiral phase transfer catalyst is novel in structure, and central nitrogen-atoms of the chiral phase transfer catalyst has good hidden performance, and therefore, the chiral phase transfer catalyst has certain special catalyzing effects, and can be suitable for requirements of catalytic reactions with various types. The chiral phase transfer catalyst prepared by the method can be applied to tert-Butyl glycinate ramification asymmetrical alkylating reaction, achieves excellent results, and is an excellent chiral phase transfer catalyst proved by practices.
Description
technical field [0001] The invention relates to chemical synthesis, in particular to the technical field of synthesis of a novel chiral phase transfer catalyst. Background technique [0002] Phase transfer catalysis occupies an important position in organic synthesis. Compared with traditional organic reactions, phase transfer catalysis has many advantages, such as mild conditions, simple and easy operation, and usually does not require anhydrous and oxygen-free operation, which can greatly simplify the reaction. operating conditions, and use cheap reagents, solvents, catalysts, catalysts are easy to recycle, environmentally friendly, and meet the requirements of green chemistry. [0003] Asymmetric phase transfer catalysis plays an important role in organic synthesis. After decades of development, asymmetric phase transfer catalysis has played an increasingly important role in asymmetric catalysis. In terms of catalyst types, the main Can be divided into phase transfer cat...
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