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Process for producing alpha-halo ketones, alpha-halohydrine and epoxides

A halogenated ketone and a production method technology are applied in the field of preparing optically active α-halogenated ketones, α-halogenated alcohols and epoxides, and can solve the problem of not establishing an industrial production method for chlorinated ketones, difficult to implement on an industrial scale, unsatisfactory, etc.

Inactive Publication Date: 2002-09-18
KANEKA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] As an industrial process, methods (1) and (2) using explosive diazomethane are unsatisfactory
Method (3) is difficult to implement on an industrial scale, partly because the reaction temperature must be below -70 °C, and partly because this method is only applicable to the special case of dibenzyl as an amino protecting group
[0013] In addition, the method (4) of reducing chloroketones to chlorohydrins is not without problems in industrial application, because the industrial production method of chloroketones has not yet been established
As far as the production of epoxides is concerned, the disadvantages of methods (5), (6) and (7) are that threo epoxides are preferentially formed and erythro epoxides cannot be obtained without special amino protecting groups

Method used

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  • Process for producing alpha-halo ketones, alpha-halohydrine and epoxides
  • Process for producing alpha-halo ketones, alpha-halohydrine and epoxides
  • Process for producing alpha-halo ketones, alpha-halohydrine and epoxides

Examples

Experimental program
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Effect test

Embodiment 1

[0088] The production of embodiment 1 phenacyl chloride (I)

[0089] Under a nitrogen atmosphere, diisopropylamine (2.42 g, 24.0 mmol) was dissolved in tetrahydrofuran (20 ml), and the solution was cooled to 0°C. To this solution was added n-butyllithium (1.6M / hexane, 13.8ml, 22.0mmol), and the mixture was stirred for 10 minutes. After cooling the solution to -30°C, monochloroacetic acid (0.946 g, 10.0 mmol) was added, and the mixture was stirred for 30 minutes. To the solution was added ethyl benzoate (0.514 g, 3.33 mmol), and the mixture was stirred at -30°C for 30 minutes. The temperature of the mixture was then raised to 25°C for 30 minutes. The reaction mixture was poured into 1N-HCl (50ml), extracted with ethyl acetate (50ml×2). The extracts were sequentially washed with saturated NaHCO 3 It was washed with aqueous solution (50ml×1) and water (50ml×1), and then dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated to give a pale y...

Embodiment 2-7

[0090] The production of embodiment 2-7 phenacyl chloride (I)

[0091] Examples 2-7 were carried out in substantially the same steps as in Example 1 with the following reaction temperatures and times.

[0092] Example

Embodiment 8

[0093] The production of embodiment 8 phenacyl chloride (I)

[0094] Diisopropylamine (0.668 g) was added to 6.67 ml of 0.9 M n-butylmagnesium chloride / tetrahydrofuran (6 mmol) under nitrogen atmosphere. The mixture was stirred at room temperature for 4 hours, then it was cooled to 0°C. A solution of 284 mg (3.0 mmol) of monochloroacetic acid and 136 mg (1 mmol) of methyl benzoate in tetrahydrofuran (5 ml) was added dropwise over 5 minutes. The mixture was stirred at 0°C for 30 minutes. The temperature was then allowed to rise to room temperature and stirred for an additional 30 minutes. The reaction mixture was poured into 1N-HCl (30ml), extracted with ethyl acetate (30ml×2). The extracts were sequentially washed with saturated NaHCO 3 It was washed with aqueous solution (30ml×1) and water (30ml×1), and then dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated to give a pale yellow oil. HPLC analysis of the oil compared to an authentic...

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Abstract

Process for the efficient production of alpha-haloketones, alpha-halohydrins and epoxides on an industrial scale. These methods include a decarboxylation of the reaction product between a carboxylic acid derivative of general formula (1) and a metal enolate prepared from an α-haloacetic acid of general formula (2) or an acceptable salt thereof to produce formula ( 3) A method for α-haloketones, a method for reducing α-haloketones (3) to produce α-halohydrins, and a method for treating α-halohydrins (11) with alkali to close the ring to produce epoxy compound method. The methods described above are particularly suitable for the production of the corresponding optically active α-haloketones, α-halohydrins and epoxides from α-amino acid derivatives. R1COA (1)

Description

technical field [0001] The present invention relates to a method for preparing α-haloketones from carboxylic acid derivatives or esters with α-haloacids, a method for preparing α-halohydrins by reducing the α-haloketones prepared above, and a method for preparing α-halohydrins by reducing the above-mentioned A method for the preparation of epoxides from α-halohydrins. [0002] More specifically, the present invention relates to the preparation of aminohaloketones, aminohalohydrins and aminoepoxides from amino acid derivatives or amino acid esters and the preparation of optically active technology for α-haloketones, α-halohydrins and epoxides. α-haloketones, α-halohydrins and epoxides prepared from optically active phenylalanine esters are important pharmaceutical intermediate compounds. Background technique [0003] The following processes for the preparation of aminohaloketones are known: [0004] (1) A method for preparing chloroketone or aminoc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/48C07C49/80C07C29/143C07C33/46C07C221/00C07C225/16C07C213/00C07C215/28C07D301/26C07D303/04C07D303/36C07C269/06C07C319/20C07C323/43
CPCC07C29/143C07C45/48C07C269/06C07C319/20C07D303/36C07C323/43C07C31/34C07C33/46C07C49/80
Inventor 西山章菅河忠志真锅肇井上健二吉田典隆
Owner KANEKA CORP
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