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Process for preparing tetrabenzyl-voglibose hydrochloride

A tetrabenzyl voglibose and preparation technology, which is applied in the field of pharmaceutical synthesis, can solve the problems of complex waste liquid treatment, environmental pollution, explosion, etc., and achieve the effects of simplified process, less three wastes, and mild reaction temperature

Inactive Publication Date: 2016-11-09
AMICOGEN CHINA BIOPHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Sodium cyanoborohydride is not only expensive, but also easy to explode under acidic conditions, releasing highly toxic gas hydrocyanic acid, polluting the environment
The waste liquid treatment after the reaction is complicated

Method used

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  • Process for preparing tetrabenzyl-voglibose hydrochloride
  • Process for preparing tetrabenzyl-voglibose hydrochloride
  • Process for preparing tetrabenzyl-voglibose hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 100mL methanol, 2g serinol, 2ml formic acid to oxocyclohexyl tetraol (10g, 18mmol), stir for 1 hour at 15°C, add (1.93g, 18mmol) 2-picoline-N-methylboron alkanes at 15°C for 16 hours. The solvent was evaporated to dryness to obtain the crude product.

[0025] Add 120mL EA to the crude product, wash twice with 40mL water and twice with 40mL 0.5M HCl aqueous solution, stir the organic phase at 15°C for 16 hours, filter with suction and dry to obtain tetrabenzyl voglibose hydrochloride 8.7 g, yield 73%.

Embodiment 2

[0027] Add 100mL ethanol, 4g serinol, 2ml acetic acid to oxocyclohexyl tetraol (10g, 18mmol), stir for 1 hour at 20°C, add (1.93g, 18mmol) 2-picoline-N-methylboron alkanes at 20°C for 16 hours. The solvent was evaporated to dryness to obtain the crude product.

[0028] Add 100mLEA to the crude product, wash twice with 50mL water and twice with 50mL 1M HCl aqueous solution, stir the organic phase at 20°C for 16 hours, filter with suction and dry to obtain 7.3g of tetrabenzyl voglibose hydrochloride, Yield 61%.

Embodiment 3

[0030] Add 100mL ethanol, 3g serinol, 2ml acetic acid to oxocyclohexyl tetraol (10g, 18mmol), stir for 1 hour at 30°C, add (1.93g, 18mmol) 2-picoline-N-methylboron alkanes at 20°C for 16 hours. The solvent was evaporated to dryness to obtain the crude product.

[0031] Add 100mLEA to the crude product, wash twice with 50mL water and twice with 50mL 0.5M HCl aqueous solution, stir the organic phase at 20°C for 16 hours, filter with suction and dry to obtain 6.2g of tetrabenzyl voglibose hydrochloride , yield 53%.

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Abstract

The invention belongs to the field of medicine synthesis, and particularly discloses a process for preparing tetrabenzyl-voglibose hydrochloride. The process particularly includes carrying out reaction on oxo-hexanaphthene tetrol and serinol to obtain reaction products and carrying out reduction on the reaction products by the aid of 2-methylpyridine-N-borane to obtain the tetrabenzyl-voglibose hydrochloride. The process has the advantages that the 2-methylpyridine-N-borane is used as a reducing agent instead of virulent and expensive sodium cyanoborohydride, accordingly, the cost of synthesis technologies can be lowered, and environmental pollution can be relieved; crude products are purified by the aid of crystallization technologies, accordingly, purification technologies can be simplified, and the product yield can be increased.

Description

technical field [0001] The invention belongs to the field of pharmaceutical synthesis, specifically a preparation process for tetrabenzyl voglibose hydrochloride, specifically a preparation process of oxocyclohexyl tetraol and serinol through the reaction of 2-picoline -N-borane reduction preparation of tetrabenzyl voglibose hydrochloride preparation process. Background technique [0002] Voglibose was first developed by Japan's Takeda Corporation, and it was first launched in Japan under the trade name Basen in 1994 for the treatment of elevated postprandial blood sugar in diabetes. Currently, there are two main chemical methods for preparing voglibose: [0003] One is to obtain voglibose by reacting Jinggang mycophenolamine and 1,3-dihydroxyacetone and reducing it with sodium cyanoborohydride, as shown below. [0004] [0005] The other is composed of (1S)-(1(hydroxyl),2,4 / 1,3)-2,3,4-tri-O-benzyl-1-C-[(benzyloxy)-methyl ]-5-Oxo-1,2,3,4-Cyclohexanethritol and serinol ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/52C07C213/02C07C249/02C07C251/20C07C213/10
CPCC07C213/02C07C213/10C07C249/02
Inventor 陈强陈伟王玲杨申勇
Owner AMICOGEN CHINA BIOPHARM CO LTD
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