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Environmentally friendly preparation method for vitamin B6

A vitamin and dioxane technology, applied in the field of pharmaceutical biochemical industry, can solve problems such as poor stability, low total yield, and many side reactions, and achieve the goal of increasing application times, high product yield, high purity, and high reactivity Effect

Active Publication Date: 2019-06-04
XINFA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the process route of this method is short, the preparation process of the raw material 4-methyl-5-ethoxyl-2-carboxy oxazole used in this method still needs to use cyclization reagents such as phosphorus oxychloride, which does not fundamentally solve the problem. Environmental issues
In addition, 4-methyl-5-ethoxy-2-carboxy oxazole has poor stability, more side reactions, and lower overall yield

Method used

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  • Environmentally friendly preparation method for vitamin B6
  • Environmentally friendly preparation method for vitamin B6
  • Environmentally friendly preparation method for vitamin B6

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Example 1: 2-n-propyl-5-cyano-4,7-dihydro-1,3-dioxin (Ⅲ1, where R 2 is n-propyl, R 3 for hydrogen) preparation

[0058] Add 300 grams of methylene chloride, 56.5 grams (0.5 moles) of 2-cyano-2-butene-1,4-diol in a 500 milliliter four-necked flask, 38.9 grams (0.54 moles) of n-butyraldehyde, 0.5 grams For p-toluenesulfonic acid, react at 30-35°C for 5 hours. Layering, the aqueous layer is extracted twice with dichloromethane (using 30 grams in total), the organic phases are combined, washed once with 20 grams of 5% aqueous sodium carbonate solution, the organic phase normal pressure distillation reclaims the dichloromethane, then underpressure distillation (120 -140°C, 5-10 mmHg) to obtain 80.6 g of 2-n-propyl-5-cyano-4,7-dihydro-1,3-dioxepin, with a GC purity of 99.7% and a yield of 96.5% .

Embodiment 2

[0059] Example 2: 2-isopropyl-5-cyano-4,7-dihydro-1,3-dioxepin (Ⅲ2, where R 2 is isopropyl, R 3 for hydrogen) preparation

[0060] Add 300 grams of chloroform, 56.5 grams (0.5 moles) of 2-cyano-2-butene-1,4-diol in a 500 milliliter four-necked flask, 38.9 grams (0.54 moles) of isobutyraldehyde, 0.5 grams of p-formaldehyde Base benzenesulfonic acid, react at 35-40°C for 5 hours. Layering, the aqueous layer was extracted twice with chloroform (using 30 grams in total), the organic phases were combined, washed once with 20 grams of 5% aqueous sodium carbonate solution, the organic phase was distilled under normal pressure to reclaim chloroform, and then distilled under reduced pressure (120-140 ° C, 5-10 mm Hg) to obtain 80.8 g of 2-isopropyl-5-cyano-4,7-dihydro-1,3-dioxin, with a GC purity of 99.9% and a yield of 96.8%.

Embodiment 3

[0061] Example 3: 2-methyl-2-ethyl-5-cyano-4,7-dihydro-1,3-dioxin (Ⅲ3, where R 2 is methyl, R 3 for ethyl) preparation

[0062] Add 300 grams of toluene, 56.5 grams (0.5 moles) of 2-cyano-2-butene-1,4-diol in a 500 milliliter four-necked flask, 39.6 grams (0.55 moles) of 2-butanone, 0.5 grams of 98 % sulfuric acid, react at 50-60°C for 4 hours. Separate the layers, extract the water layer twice with toluene (using 30 grams in total), combine the organic phases, wash once with 20 grams of 5% aqueous sodium carbonate solution, and reclaim the toluene by atmospheric distillation of the organic phase, then distill under reduced pressure (120-140 ° C, 5-10 mm Hg) to obtain 79.6 grams of 2-methyl-2-ethyl-5-cyano-4,7-dihydro-1,3-dioxin, GC purity 99.6%, yield 95.3% .

[0063] 2. Preparation of 2,2-disubstituent-5-cyano-6-formyl-1,3-dioxane (IV):

[0064]

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Abstract

The invention relates to an environmentally friendly preparation method for vitamin B6. The method comprises the following steps: carrying out a condensation reaction on a carbonyl compound and 2-cyano-2-cis-butene-1,4-diol which is used as a starting material, protecting hydroxyl groups to obtain 2,2-disubstituted-5-cyano-4,7-dihydro-1,3-dioxepine, carrying out a formylation reaction on the 2,2-disubstituted-5-cyano-4,7-dihydro-1,3-dioxepine, carbon monoxide and hydrogen to prepare 2,2-disubstituted-5-cyano-6-formyl-1,3-dioxetpin, condensing the 2,2-disubstituted-5-cyano-6-formyl-1,3-dioxetpin and 2-aminopropionate or its hydrochloride, and removing the carbonyl compound to prepare the vitamin B6. The method does not use a 4-methyl-5-alkoxyoxazole intermediate which is expensive and generates a large amount of wastewater in the production process, so the method has the advantages of environmentally friendly process, high reaction selectivity, high product purity, high atom economy, and suitableness for industrial production.

Description

technical field [0001] The invention relates to a vitamin B 6 The green and environment-friendly preparation method belongs to the technical field of pharmaceutical biochemical industry. Background technique [0002] Vitamin B 6 It is one of the essential vitamins for the human body and plays a key role in the growth of animals, so it is widely used in the fields of medicine, food, feed additives and cosmetics industries. Vitamin B 6 (referred to as VB 6 ) exists in nature in three forms: pyridoxine, pyridoxal and pyridoxamine. Under certain conditions, the three can be transformed into each other in vivo. Industrially synthesized vitamin B 6 Usually pyridoxine hydrochloride. [0003] In industry, vitamin B is usually produced by chemical synthesis 6 , as mentioned in U.S. Patent US3227721, 2-methyl-3-hydroxy-pyridine-4,5-dicarboxylic acid diethyl ester uses lithium tetrahydrogen as a reducing agent to prepare vitamin B 6 , but the amount of lithium tetrahydrogen is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/67
Inventor 戚聿新李新发王涛吕强三于大伟
Owner XINFA PHARMA
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