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Synthetic method of (R)-2-methyl-4-nitro-1-butanol

A synthesis method, the technology of nitro-n-butyraldehyde, is applied in the field of synthesis of -2-methyl-4-nitro-1-butanol to achieve cost-saving effect

Inactive Publication Date: 2014-01-01
CHEMFUTURE PHARMATECH JIANGSU
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The purpose of the present invention is to overcome the problem that existing (R)-2-methyl-4-nitro-1-butanol synthesis method needs to carry out the problem of racemate resolution, and provides a kind of (R)-2 -The synthetic method of methyl-4-nitro-1-butanol

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  • Synthetic method of (R)-2-methyl-4-nitro-1-butanol
  • Synthetic method of (R)-2-methyl-4-nitro-1-butanol

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Experimental program
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Effect test

Embodiment 1

[0025] (1) Add 120.0g (1.042mol) (S)-proline to 1.2L tetrahydrofuran (THF), cool down to 15°C, slowly add 648 ml phosgene toluene solution (COCl 2 1.93mol / L, 1.25mol), stirred for 1 hour, then raised the temperature to 40°C, stirred for 30 minutes, then lowered the temperature to 20°C, concentrated the reaction solution to 160ml by distillation under reduced pressure, added 1.2L tetrahydrofuran, and then lowered the temperature to 0°C , then added dropwise the triethylamine of 145.2ml (1.042mol) in 15 minutes, stirred for 30 minutes, filtered, and the filter residue was washed with tetrahydrofuran, collected the filtrate and the washings, and removed the solvent by distillation under reduced pressure to obtain the product 139.6g (S)- Proline-N-carboxy-anhydride (namely compound 3), the yield is 95%.

[0026] (2) Cool 1.6L of phenylmagnesium chloride (3.2mol) in tetrahydrofuran (2mol / L) to -10°C, and slowly add 600mL of (S)-proline-N-carboxy-anhydride (139.6g , 0.99mol) in t...

Embodiment 2

[0030] (1) Add 12.0g (0.1mol) (S)-proline into 120ml tetrahydrofuran, cool down to 20°C, slowly add 54ml phosgene toluene solution (COCl 2 1.93mol / L, 0.1mol), stirred for 0.5 hours, then raised the temperature to 30°C, stirred for 45 minutes, then lowered the temperature to 20°C, concentrated the reaction solution to 16ml by distillation under reduced pressure, added 120ml of tetrahydrofuran, and then lowered the temperature to 5°C, Then 6.67ml (0.05mol) of triethylamine was added dropwise within 15 minutes, stirred for 30 minutes, filtered, the filter residue was washed with tetrahydrofuran, the filtrate and washings were collected, and the solvent was distilled off under reduced pressure to obtain the product 11.9g (S)-proline Amino acid-N-carboxy-anhydride in the ring (namely compound 3), the yield is 80.9%.

[0031](2) Cool 106ml of phenylmagnesium chloride solution in tetrahydrofuran (2mol / L, 0.2mol) to -10°C, and slowly add 51.15mL of (S)-proline-N-carboxy-anhydride (1...

Embodiment 3

[0035] (1) Add 12.0g (0.1mol) (S)-proline into 120ml tetrahydrofuran, cool down to 15°C, slowly add 81 ml phosgene toluene solution (COCl 2 1.93mol / L, 0.15mol), stirred for 0.5 hours, then raised the temperature to 40°C, stirred for 30 minutes, then lowered the temperature to 15°C, concentrated the reaction solution to 16ml by distillation under reduced pressure, added 120ml of tetrahydrofuran, and then lowered the temperature to 0°C, Then within 15 minutes, 16.68ml (0.125mol) of triethylamine was added dropwise, stirred for 30 minutes, filtered, the filter residue was washed with tetrahydrofuran, the filtrate and washings were collected, and the solvent was distilled off under reduced pressure to obtain the product 12.7g (S)-proline Amino acid-N-carboxy-anhydride in the ring (namely compound 3), the yield is 86.3%.

[0036] (2) Cool 159ml of phenylmagnesium chloride solution in tetrahydrofuran (2mol / L, 0.315mol) to -10°C, and slowly add 54.58mL of (S)-proline-N-carboxy-anhyd...

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Abstract

The invention discloses a synthetic method of (R)-2-methyl-4-nitro-1-butanol. The method comprises the following steps that firstly, (S)-alpha, alpha-diphenyl-pyrrolidinemethanol is reacted with trimethylsilyl trifluoromethanesulfonate under the catalyzing action of triethylamine to obtain (S)-2-(1, 1-diphenyl-1-trimethylsilanolate) methyl pyrrolidine, and secondly, (S)-2-(1, 1-diphenyl-1- trimethylsilanolate) methyl pyrrolidine is reacted with acetaldehyde, 3-nitrobenzoic acid and nitro ethylene in a mixing mode to obtain (S)-2-methyl-4-nitro n-butanal, and the (S)-2-methyl-4-nitro n-butanal is reduced to obtain (R)-2-methyl-4-nitro-1-butanol. By means of the method, the (R)-2-methyl-4-nitro-1-butanol can be obtained directly instead of racemate, the racemate is prevented from being resolved, cost is saved, and the yield is 50%.

Description

technical field [0001] The invention relates to a synthesis method of (R)-2-methyl-4-nitro-1-butanol. Background technique [0002] (R)-2-Methyl-4-nitro-1-butanol is an important intermediate in biomedicine and has a wide range of biological activities, but it is rarely distributed in nature. The previous chemical synthesis methods often have long synthetic routes. , the raw material is expensive, the yield is low and other disadvantages, it is not suitable for large-scale industrial production, and the reaction is a racemate, which cannot be synthesized directionally, and the obtained racemate needs to be resolved to obtain (R)-2-formazan Base-4-nitro-1-butanol. Contents of the invention [0003] The purpose of the present invention is to overcome the problem that existing (R)-2-methyl-4-nitro-1-butanol synthesis method needs to carry out the problem of racemate resolution, and provides a kind of (R)-2 - Synthesis of methyl-4-nitro-1-butanol. [0004] The technical sch...

Claims

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Application Information

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IPC IPC(8): C07C205/15C07C201/12
Inventor 徐骏顾喜丰吴妤萱
Owner CHEMFUTURE PHARMATECH JIANGSU
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