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Preparation method for miglitol

A technology of miglitol and alcoholic solvent, applied in the field of compound preparation, can solve the problems of cumbersome steps, high synthesis cost, difficult purification and the like

Inactive Publication Date: 2018-03-02
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The currently reported Miglitol synthesis processes mainly include: Chemical total synthesis method (Tetrahedron Lett., 2000, 41, 7313), this method has cumbersome steps, many by-products, and difficult purification; Using glucosamine or N-substituted glucosamine as raw materials to prepare miglitol (EP49858, DE3024901, EP55431), this method does not involve the preparation of glucosamine or N-substituted glucosamine; Miglitol (US4611058) is synthesized from tetrahydrofuranose derivatives by borohydride reduction. This method has a low yield and high synthesis cost, and is not suitable for industrial production

Method used

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  • Preparation method for miglitol

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Experimental program
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Effect test

Embodiment 1

[0021] In a 1L autoclave, add 400 ml 6-deoxy-6-hydroxyethylamino-α-L-sorbose cell resting solution (containing 6-deoxy-6-hydroxyethylamino-α-L-sorbose 40 g), 40 ml ethanol, 1.6 g 10% Pd / C (water content 50%), replace the air with hydrogen, maintain the pressure at 1~1.5 MPa, and react at 25 °C for 7 hours, N 2 Palladium carbon was removed by pressure filtration (for the next batch of reactions), concentrated, ethanol crystallized, suction filtered, washed, and vacuum-dried to obtain 34 g of miglitol crystals, with a yield of 92% and a purity of 99.1% (HPLC detection).

[0022] The spectrum characterization of miglitol crystals: 1 H NMR (600 MHz, D 2 O- d 6 ) δ: 3.81 (ddd, J 1 = 2.4Hz, J 2 = 14.4Hz, J 3 = 15.6 Hz, 2H), 3.71~3.64 (m, 2H), 3.49~3.45 (m, 1H), 3.30(t, J = 9 Hz, 1H), 3.20 (t, J = 9 Hz, 1H), 3.03~3.00 (m, 1H), 2.90~2.86 (m,1H), 2.68~2.64 (m, 1H), 2.31~2.24 (m, 2H); 13 C NMR (100MHz, D 2 O- d 6 ) δ: 78.23,69.92, 68.70, 65.55, 57.86, 57.56, 56.04, 52.7...

Embodiment 2

[0024] In a 1L autoclave, add 400 ml 6-deoxy-6-hydroxyethylamino-α-L-sorbose cell resting solution (containing 6-deoxy-6-hydroxyethylamino-α-L-sorbose 40 g), 200 ml methanol, 4 g Raney nickel, replace air with hydrogen, maintain pressure 1~2 MPa, temperature 27°C, react for 8 hours, N 2 Press filtration to remove Raney nickel (for the next batch of reactions), concentration, ethanol crystallization, suction filtration, and vacuum drying to obtain 35 g of miglitol crystals with a yield of 94% and a purity of 99.0% (by HPLC).

Embodiment 3

[0026] In a 1L autoclave, add 400 ml 6-deoxy-6-hydroxyethylamino-α-L-sorbose cell resting solution (containing 6-deoxy-6-hydroxyethylamino-α-L-sorbose 40 g), 200 ml isopropanol, 4 g 10% platinum carbon (water content 50%), replace air with hydrogen, maintain pressure 1.5~2 MPa, temperature 27 °C, react for 8 hours, N 2 Press filtration to remove platinum carbon (for the next batch of reactions), concentration, ethanol crystallization, suction filtration, and vacuum drying to obtain 35 g of miglitol crystals with a yield of 94% and a purity of 99.0% (HPLC detection).

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Abstract

The invention discloses a preparation method for miglitol. The method comprises the following steps: selecting 6-deoxy-6-hydroxyethylamino-alpha-L-sorbose as a raw material, adding an alcohol solvent,performing a catalytic hydrogenation reaction under a certain pressure condition in the presence of a hydrogen gas, then performing pressure filtration, performing concentration, performing crystallization, performing vacuum filtration, performing washing, and performing vacuum drying to obtain the miglitol crystal. According to the invention, the reaction time is 7-8h, the temperature is 20-30 DEG C, the yield is greater than 90%, and the purity is greater than 99% (HPLC detection); and the reagents used by the method are green, environmentally friendly, pollution-free, economical and practical, the reaction yield is high, and the method is simple and convenient for operation, and suitable for industrialized mass production.

Description

technical field [0001] The invention relates to a preparation method of a compound, in particular to a preparation method of miglitol, a medicine for treating type II diabetes. Background technique [0002] Miglitol (Miglitol) is a new type of anti-diabetic drug launched by Bayer in 1997. It is a new type of intestinal α-glucosidase inhibitor discovered from the bacillus broth medium. It is the parent modified product of 1-deoxynojirimycin and belongs to the N-substituted-1-deoxynojirimycin type. Similar to glucose. The chemical name is 1-(2-hydroxyethyl)-2-(hydroxymethyl)-3,4,5-piperidine triol; melting point: 146°C, optical rotation [α]D20=-8(C,1 ,CH 3 OH), the structural formula is as follows: [0003] [0004] Diabetes is the most common disease caused by endocrine and metabolic disorders, mainly divided into type I diabetes and type II diabetes (non-insulin-dependent diabetes mellitus, NIDD). Among them, type Ⅱ diabetes is the main one. The current treatment me...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/46
CPCC07D211/46
Inventor 帅棋宋平原生英涛储消和苏为科吴杰群
Owner ZHEJIANG UNIV OF TECH
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