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Method for preparing (R)-3-amino piperidine hydrochloride

A technology of bishydrochloride and aminopiperidine, which is applied in the field of medicine, can solve problems such as affecting yield, increasing production cost, and improving production equipment requirements, and achieves the effect of low cost and short synthetic route

Inactive Publication Date: 2014-06-18
NANYANG INST OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] However, there are several problems in the existing preparation technology of (R)-3-aminopiperidine dihydrochloride: ①The resolution method is needed in the synthesis process, which affects the yield
② Raw materials are expensive
③Reaction conditions need to be carried out at low temperature, which increases the requirements for production equipment and increases production costs

Method used

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  • Method for preparing (R)-3-amino piperidine hydrochloride
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  • Method for preparing (R)-3-amino piperidine hydrochloride

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Embodiment 1

[0030] A preparation method of (R)-3-aminopiperidine dihydrochloride, comprising the following reaction steps:

[0031] ① Synthesis of N-tert-butoxycarbonyl-D-glutamic acid dimethyl ester (APD1):

[0032]

[0033] Dissolve 20g of D-glutamic acid in 120ml of MeOH (ice bath) with stirring, add 32g of SOCl 2 Keep the temperature below 30°C. After the addition, raise the temperature to 30±5°C, stir for 6±0.5h, take a sample and pass the high-performance liquid chromatography test, stop the reaction when the monomer conversion rate exceeds 95%, and remove the solvent under reduced pressure. Add 50mlH 2 O and 50ml Dioxane, placed in an ice bath to cool, add 27.3gTEA and 32.2g (Boc) 2 O, after the addition is complete, remove the ice bath and heat to 30±5°C, and stir for 5-6 hours. The reaction of the intermediate is detected by LC-MS, and the reaction is stopped. The organic solvent was removed and extracted with 2 x 150ml EA. Washed by brine, Na 2 SO 4 Drying gave an oil. ...

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Abstract

The invention discloses a method for preparing (R)-3-amino piperidine hydrochloride. D-glutamic acid is taken as a starting material, and the (R)-3-amino piperidine hydrochloride is obtained by reaction in the following five steps: (1) hydroxyl esterification and amido Boc protection; (2) ester reduction; (3) hydroxyl activation; (4) cyclization; (5) amino Boc removal protection. The preparation method disclosed by the invention is short in synthetic route and low in cost, and industrial production can be achieved.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a preparation method of a medicine intermediate (R)-3-aminopiperidine dihydrochloride. Background technique [0002] (R)-3-aminopiperidine dihydrochloride is mainly used in the synthesis of dipeptidyl peptidase-IV (DPP-IV) inhibitors. It is a new type of high value-added pharmaceutical intermediate, which is expensive. [0003] The traditional synthesis method of (R)-3-aminopiperidine dihydrochloride is generally resolved by synthesizing racemic 3-aminopiperidine and its hydrochloride, or directly synthesizing (R)- 3-aminopiperidine and its hydrochloride. Through the retrieval of domestic and foreign documents, its synthetic method is mainly as follows: [0004] Route 1: Using 3-aminopiperidine as a starting material, obtain (R)-3-aminopiperidine dihydrochloride through hydrogenation reduction, resolution and salification. [0005] Route 2: Using nicotinamide as raw materia...

Claims

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Application Information

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IPC IPC(8): C07D211/56C07D211/02
CPCC07D211/02C07D211/56
Inventor 李朝艳宋伟徐雪丽闫卫红曹英寒
Owner NANYANG INST OF TECH
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