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A kind of synthetic method of 1-tert-butoxycarbonyl-2-methyl-4-piperidone

A technology of tert-butoxycarbonyl and 1-cbz-2-, which is applied in the field of organic synthesis, can solve the problems of low total yield, danger, and long route, and achieve the effects of easy scale-up production, increased yield, and low energy consumption

Inactive Publication Date: 2016-08-03
甘肃科瑞生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The first method has a long route and the total yield is very low, less than 21%. The second method uses tert-butyllithium, which is dangerous and not easy to scale up production. The third method will produce A by-product with a molar ratio of 1:1 to the reaction product, difficult to purify

Method used

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  • A kind of synthetic method of 1-tert-butoxycarbonyl-2-methyl-4-piperidone
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  • A kind of synthetic method of 1-tert-butoxycarbonyl-2-methyl-4-piperidone

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Embodiment 1

[0043] The synthetic method of 1-tert-butoxycarbonyl-2-methyl-4-piperidone comprises the following steps:

[0044] (1) Dissolve 150 grams of 4-methoxy (1.375 mol) pyridine in 1850 ml of tetrahydrofuran, add 19 ml (1.375 mol) of triethylamine, cool down to minus 40 ° C, and then dropwise add 235 grams (1.375 mol) Cbz-Cl, after the dropwise addition, keep minus 40°C for 20 minutes, under the protection of nitrogen, add dropwise 692ml of ether solution containing 3mol / L methylmagnesium bromide, after the dropwise addition is completed, return to room temperature, and react at room temperature for 2 Hours, TLC, the raw material has reacted completely, quenched the reaction with 500ml of 1Mol / L hydrochloric acid, extracted 3 times with 300 ml of ethyl acetate respectively, combined the organic phases, washed once with saline, dried over sodium sulfate, and evaporated the solvent to obtain reddish brown 323.8 g of the oily substance is 1-Cbz-2-methyl-3,4-dihydro-4-piperidone, and th...

Embodiment 2

[0048] The synthetic method of 1-tert-butoxycarbonyl-2-methyl-4-piperidone comprises the following steps:

[0049] (1) Dissolve 900 grams of 4-methoxypyridine (8.25mol) in 10 liters of tetrahydrofuran, add 114ml (8.25mol) of triethylamine, cool down to minus 40°C, and then dropwise add 1410 grams (8.25mol) Cbz-Cl, after the dropwise addition, keep minus 40°C for 30 minutes, under the protection of nitrogen, add dropwise 4152ml of ether solution containing 3mol / L methylmagnesium bromide, after the dropwise addition is completed, return to room temperature, and react at room temperature for 2 Hours, TLC, the raw material has reacted completely, quenched the reaction with 2500ml of 1Mol / L hydrochloric acid, extracted 3 times with 1500ml of ethyl acetate respectively, combined the organic phases, washed once with saline, dried over sodium sulfate, and evaporated the solvent to obtain reddish brown 1950 g of the oily substance is 1-Cbz-2-methyl-3,4-dihydro-4-piperidone, and the yie...

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Abstract

The invention discloses a synthesis method of 1-tertbutyloxycarbonyl-2-methyl-4-piperidone. The synthesis method comprises the following steps: step one, synthesis of 1-Cbz-2-methyl-3,4-dihydro-4-piperidone; step two, synthesis of 1-Cbz-2-methyl-4-piperidone; step three, synthesis of 1-tertbutyloxycarbonyl-2-methyl-4-piperidone. The synthesis method takes 4-methoxypyridine as the raw material, then subjects the 4-methoxypyridine to react with Cbz-Cl at a low temperature, then subjects the reaction product to carry out addition reactions with methylmagnesium chloride, reduces the reaction product with zinc powder, and finally hydrogenates the reduction reaction product. Compared to the prior art, the whole synthesis route has the advantages of easiness in production amplification, suitability for industrial and massive production, low energy consumption, and great improvement on yield.

Description

technical field [0001] The invention relates to a synthesis method of 1-tert-butoxycarbonyl-2-methyl-4-piperidone, which belongs to the field of organic synthesis. Background technique [0002] 1-tert-butoxycarbonyl-2-methyl-4-piperidone is a very useful pharmaceutical intermediate, but the current methods of synthesizing 3-hydroxy-azetidine hydrochloride are as follows: [0003] First method route: [0004] [0005] Second method route: [0006] [0007] Third method route: [0008] [0009] The first method has a long route and the total yield is very low, less than 21%. The second method uses tert-butyllithium, which is dangerous and not easy to scale up production. The third method will produce A by-product with a molar ratio of 1:1 to the reaction product, difficult to purify. Contents of the invention [0010] The technical problem to be solved by the present invention is to overcome existing defects and provide a synthetic method of 1-tert-butoxycarbony...

Claims

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Application Information

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IPC IPC(8): C07D211/74
CPCC07D211/74
Inventor 詹智年
Owner 甘肃科瑞生物科技有限公司
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