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Synthetic process of anti-hyperglycemic drug intermediate R-3-amino-piperidine dihydrochloride

An anti-hyperglycemia, R-3- technology, applied in the production of bulk chemicals, organic chemistry, etc., can solve the problems of low total yield and limited application, and achieve high total yield, cheap raw materials, and atom economy Good results

Inactive Publication Date: 2019-10-25
苏州汉德创宏生化科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] This route avoids the above-mentioned shortcomings, but the total yield of the last two steps is on the low side, which limits its application in industrial production

Method used

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  • Synthetic process of anti-hyperglycemic drug intermediate R-3-amino-piperidine dihydrochloride
  • Synthetic process of anti-hyperglycemic drug intermediate R-3-amino-piperidine dihydrochloride
  • Synthetic process of anti-hyperglycemic drug intermediate R-3-amino-piperidine dihydrochloride

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Embodiment Construction

[0051] The present invention will be further described below in conjunction with specific embodiments. The following examples are only used to illustrate the technical solution of the present invention more clearly, but not to limit the protection scope of the present invention.

[0052] 1, the preparation of dimethyl (tert-butoxycarbonyl)-L glutamate:

[0053] Add 147g (1mol) of L-glutamic acid and 588g of methanol into a three-necked flask; stir at room temperature, and slowly add 240g (2.02mol) of thionyl chloride into the reaction system through the dropping funnel; The internal temperature was raised to 55° C., and the reaction was kept at 55° C. for 2 hours; the end of the reaction was monitored by thin layer chromatography (TLC). After the reaction was completed, the solvent was evaporated under reduced pressure, and the obtained crude product was dissolved in water (825 g). Take 165g of solid sodium bicarbonate and add it into water to adjust the pH to 7-8, then add ...

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Abstract

The invention relates to a synthetic process of an anti-hyperglycemic drug intermediate R-3-amino-piperidine dihydrochloride. The synthetic process comprises the steps: using inexpensive L-glutamic acid as a starting material, and performing esterification, amino protection, reduction, hydroxyl protection, substitution, cyclization and removal of protecting groups for amino groups so as to obtainthe R-3-amino-piperidine dihydrochloride. Compared with the prior art, the synthetic process has cheap and easily available raw materials, good selectivity, good atomic economy, high total yield and mild reaction conditions, and is suitable for industrial production.

Description

technical field [0001] The invention relates to the field of pharmaceutical intermediates, in particular to a synthesis process of R-3-amino-piperidine dihydrochloride, an antihyperglycemic pharmaceutical intermediate. Background technique [0002] R-3-amino-piperidine dihydrochloride is an important drug intermediate, and the synthesis of linagliptin, alogliptin, linagliptin, etc. requires the use of R-3-amino-piperidine dihydrochloride Hydrochloride is used as an intermediate, so the synthesis of this compound is widely used in the field of medicine. [0003] The traditional methods of synthesizing R-3-amino-piperidine dihydrochloride have obvious shortcomings. For example, the reduction reaction of some relatively complex precursor molecules containing R-3-amino-piperidine framework is carried out to obtain R-3-amino-piperidine dihydrochloride, and the reaction in the conversion requires relatively high temperature and oxidant, or The use of highly toxic pyridine deriva...

Claims

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Application Information

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IPC IPC(8): C07D211/56
CPCC07D211/56Y02P20/55
Inventor 茅仲平马东旭魏华
Owner 苏州汉德创宏生化科技有限公司
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