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Preparation method of mono-chiral metallic organic frame material with function of splitting chiral amine

A metal-organic framework and chiral amine technology, which is used in the preparation of monochiral metal-organic frameworks (MOFs) to achieve the effects of stable internal structure, cheap reaction raw materials and low reaction temperature

Inactive Publication Date: 2015-02-25
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The operation of the present invention is relatively simple, easy to operate, and the separation effect of chiral amine is ideal

Method used

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  • Preparation method of mono-chiral metallic organic frame material with function of splitting chiral amine
  • Preparation method of mono-chiral metallic organic frame material with function of splitting chiral amine
  • Preparation method of mono-chiral metallic organic frame material with function of splitting chiral amine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Step 1, (S)-3,3'-di-tert-butyl-5,5'-dibromo-6,6'-dimethyl-2,2'-dihydroxy-1,1'-biphenyl [Eur.J.Org.Chem.2010, 3027] (1.0g, 2mmol), 5-pinacol ester methyl isophthalate [Cryst.Growth Des., 2010, 2775] (1.7g, 5.6mmol) , potassium phosphate trihydrate (1.9g, 9mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (80mg, 0.1mmol) was placed in a reaction flask, and added under nitrogen protection Dioxane / water = 9:1 (60mL) mixed solvent, reflux for 10 hours and then cool to room temperature, extract the reaction solution several times with ethyl acetate, combine the organic phases and wash with saturated sodium chloride for several times After drying with anhydrous sodium sulfate, it was filtered with a Buchner funnel and spin-dried, and the crude product was separated and purified by column chromatography (silica gel column, the eluent was petroleum ether:ethyl acetate=10:1) to obtain the target product (S )-3,3'-di-tert-butyl-5,5'-bis(3,5-dimethoxycarbonylphenyl...

Embodiment 2

[0052]After solvent exchange, 30 mg of the monochiral metal-organic framework material with chiral separation function obtained in Step 3 of Example 1 was placed under vacuum at 80°C for 2 hours, and then dissolved in 5 mL of exosome at -10°C. Racemic 1-(4-fluorophenyl)ethylamine soaked in methanol for one day, filtered through a Buchner funnel, washed several times with methanol, then soaked in tetrahydrofuran for one day, filtered through a Buchner funnel, and the filtrate was derivatized with benzoyl chloride Using a Chiralcel OD-H liquid-phase chiral separation column, at 25°C, n-hexane / isopropanol=90 / 10, and a flow rate of 0.6mL / min, the ee value of chiral amine separation can reach 98.7%, as shown in image 3 shown. image 3 The analysis results in are as follows:

[0053]

Embodiment 3

[0055] After solvent exchange, 30 mg of the monochiral metal-organic framework material with chiral separation function obtained in Step 3 of Example 1 was placed under vacuum at 80°C for 2 hours, and then dissolved in 5 mL of exosome at -10°C. Soak racemic 1-(4-bromophenyl)ethylamine in methanol for one day, filter with Buchner funnel, wash with methanol several times, then soak in tetrahydrofuran for one day, filter with Buchner funnel, and derivatize the filtrate with benzoyl chloride Using a Chiralcel OD-H liquid-phase chiral separation column, at 25°C, n-hexane / isopropanol=90 / 10, and a flow rate of 1.0mL / min, the measured chiral amine separation ee value reaches 91.5%, such as Figure 4 shown. Figure 4 The analysis results in are as follows:

[0056]

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Abstract

The invention provides a preparation method of a mono-chiral metallic organic frame material with a function of splitting chiral amine. The method comprises the following steps of: dissolving manganese salt and mono-chiral ligand (S)-3,3'-di-tert-butyl-5,5'-di(3,5-dicarboxylphenyl)-6,6'-dimethyl-2,2'-dihydroxyl-1,1'-bipheny into methanol and N,N-dimethyl formamide according to certain proportions, stirring for 10 minutes and then heating up to 80-85 DEG C, reacting for about 24 hours to generate colorless needle-like crystals, and then washing with aether to obtain the structurally stable mono-chiral metallic organic frame material with the function of splitting the chiral amine. The preparation method provided by the invention has the characteristics that the preparation condition is mild, the operation is simple, the separation ee value of the chiral amine is higher than 90%, and the chiral amine is reusable.

Description

technical field [0001] The invention relates to a preparation method in the technical field of chemical industry, in particular to a preparation method of monochiral metal-organic framework materials (MOFs) with the function of splitting chiral amines. Background technique [0002] In recent years, with the development of solid-state chemistry, monochiral metal-organic framework materials have shown broad application prospects in the fields of chiral recognition and separation, chiral fluorescence, and heterogeneous asymmetric catalysis. Studies have shown that as long as the pore size and shape of MOFs match the target molecules, the framework materials with amphiphilic holes may show strong affinity for those amphiphilic guest molecules, and such MOFs can target Some chiral molecules undergo chiral recognition and separation. At present, the filling materials of chiral gas chromatographic columns used for the separation of chiral amines are mainly cyclodextrin derivatives...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F13/00C07C65/105C07C27/02C07B57/00C07C209/88C07C211/27C07C211/29C07C211/07C07C213/10C07C217/60B01J20/22B01J20/30B01D15/08
Inventor 彭永武崔勇
Owner SHANGHAI JIAO TONG UNIV
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