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(R)-1-benzyl-3-methyl-1,2,3,6-tetrahydropiperidyl synthetic method

A technology of tetrahydropiperidine and a synthetic method, applied in directions such as organic chemistry, to achieve the effects of saving production costs, simple post-processing, and shortening time

Active Publication Date: 2015-06-17
HANGZHOU ALLSINO CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For the preparation of (R)-1-benzyl-3-methyl-1,2,3,6-tetrahydropiperidine, there are no domestic and foreign data reports

Method used

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  • (R)-1-benzyl-3-methyl-1,2,3,6-tetrahydropiperidyl synthetic method

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Embodiment 1

[0032] Ethyl di-o-tolyloxyphosphoryl acetate (4.29g, 12.3mmol) was dissolved in 40mL THF, cooled to -10°C under nitrogen protection. Potassium tert-butoxide (1.52g, 13.5mmol) was added in portions. After the addition was complete, the reaction was incubated for 2 hours. (2S)-3-tert-butyldimethylsilyloxy-2-methylpropanal (I) (2g, 9.9mmol) was configured into a THF solution with a mass percent concentration of 50%, and slowly added dropwise to the reaction in the liquid. After dropping, keep warm for 2 hours. After GC detection, the reaction was completed and quenched by adding water-saturated ammonium chloride aqueous solution. Separate the organic phase, remove the solvent, then add petroleum ether and water, extract and separate the layers. The aqueous phase was extracted twice with petroleum ether, and the organic phases were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. Pave silica gel in sand core funnel, the solution after drying is s...

Embodiment 2

[0036]Dissolve ethyl di-2-tert-butylphenylphosphoryl acetate (23.3g, 53.9mmol) in 117mL THF, and lower the temperature to -15°C under nitrogen protection. Add potassium tert-butoxide (6.05g, 53.9mmol) in batches . After the addition was complete, the reaction was incubated for 1 hour. (2S)-3-tert-butyldimethylsilyloxy-2-methylpropanal (I) (8.4g, 41.5mmol) was configured into a THF solution with a mass percentage concentration of 20%, and slowly added dropwise to in the reaction solution. After dropping, keep warm for 3 hours. After GC detection, the reaction was completed and quenched by adding water-saturated ammonium chloride aqueous solution. Separate the organic phase, remove the solvent, then add petroleum ether and water, extract, and separate layers. The aqueous phase was extracted twice with petroleum ether, and the organic phases were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. Pave silica gel in sand core funnel, the solution ...

Embodiment 3

[0040] Dissolve triethyl phosphoacetate (13.95 g, 62.2 mmol) in 100 mL of THF, and lower the temperature to -5°C under nitrogen protection. Add potassium tert-butoxide (1.52 g, 13.5 mmol) in portions. After the addition, the reaction was incubated for 2 hours. (2S)-3-tert-butyldimethylsilyloxy-2-methylpropanal (I) (9g, 44.5mmol) was configured into a THF solution with a mass percent concentration of 30%, and slowly added dropwise to the reaction in the liquid. After dropping, keep warm for 2 hours. After GC detection, the reaction was completed and quenched by adding water-saturated ammonium chloride aqueous solution. Separate the organic phase, remove the solvent, then add petroleum ether and water, extract and separate the layers. The aqueous phase was extracted twice with petroleum ether, and the organic phases were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. Pave silica gel in sand core funnel, the solution after drying is sucked and...

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Abstract

The invention provides a (R)-1-benzyl-3-methyl-1,2,3,6-tetrahydropiperidyl synthetic method, Which comprises the following steps: a)a substance shown in a formula I) is reacted to phosphate ester through Horner-Wadsworth-Emmons to generate a compound shown in a formula (II); b)the compound shown in the formula (II) is reduced by diisobutylaluminium hydride to obtain alcohol, and a deprotection reaction through concentrated hydrochloric acid-ethanol to obtain a compound shown in a formula (III); and c)the compound shown in the formula (III) is reacted through methylsulfonyl chloride or toluenesulfonyl chloride to obtain sulphonate or tosylate, and is performed with a benzylamine cyclization reaction in alcohol to obtain a compound shown in a formula (IV). The synthetic method is characterized in that initial raw materials, technical routes and post-treatment process are different, and the synthetic method has the advantages of simple and easily available raw materials, low cost and simple operation.

Description

technical field [0001] The invention relates to the technical field of organic compound synthesis, in particular to a synthesis method of (R)-1-benzyl-3-methyl-1,2,3,6-tetrahydropiperidine. Background technique [0002] (R)-1-benzyl-3-methyl-1,2,3,6-tetrahydropiperidine can be used as an intermediate in the synthesis of kinase inhibitors or as a chiral source for the synthesis of organic compounds or drugs (WO2005077932A , US2010056576A1, US2012225062A1, etc.). For the preparation of (R)-1-benzyl-3-methyl-1,2,3,6-tetrahydropiperidine, there are no domestic and foreign data reports. [0003] In view of this, it is necessary to develop a synthetic method for (R)-1-benzyl-3-methyl-1,2,3,6-tetrahydropiperidine. Contents of the invention [0004] The invention provides a synthetic method of (R)-1-benzyl-3-methyl-1,2,3,6-tetrahydropiperidine. Different, its raw materials are simple and easy to get, the cost is low, and the operation is simple. [0005] Technical scheme of th...

Claims

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Application Information

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IPC IPC(8): C07D211/70C07D211/02
CPCC07D211/02C07D211/70
Inventor 闻建明方卫国胡建锋
Owner HANGZHOU ALLSINO CHEM
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