Synthesis method of 4-(toluene-4-sulfonyl oxygen) piperidine-1- carboxylic tert-butyl ester
A technology of tert-butyl carboxylate and synthesis method, which is applied in the direction of organic chemistry, can solve the problems of high price and low catalytic yield, and achieve the effects of improved production safety factor, good reaction repeatability and mild reaction conditions
Inactive Publication Date: 2012-08-01
LANZHOU WANHAO BIOLOGICAL TECH
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Problems solved by technology
The method is simple to operate and the yield is high, but the disadvantage is that the raw materials 4-hydroxypiperidine and 2-mercapto-4,6-dimethylpyrimidine are relatively expensive.
The disadvantage of this method is that the catalytic yield is low, and the raw material 4-hydroxypyrimidine cannot be bought on the market.
Method used
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Embodiment 1
[0077] Using 1-benzyl-4-piperidone as the starting material, the intermediate A is obtained by hydrogenation and reduction reaction with sodium borohydride, and then the intermediate product B is obtained by catalytic debenzylation with palladium carbon, and B is in triethylamine alkaline solution The product C is obtained by reacting with Boc anhydride, and the final product D is obtained by condensation reaction of C with p-toluenesulfonyl chloride.
[0078] The first step reaction is hydrogenation reduction reaction. During the preparation of intermediate A, the tetrahydroboron ion attacks the positively charged carbon atom in the unsaturated bond, and is reduced due to the transfer of a strong reducing hydride ion. A complex is generated in an aprotic solvent, and an alcohol is obtained in a protic solvent. From A to B is a catalytic hydrogenolysis reaction. The benzyl group is directly connected to the N on piperidine. Due to the strong electronegativity and partial neg...
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The invention discloses a synthesis method of 4-(toluene-4-Sulfonyl oxygen) piperidine-1- carboxylic tert-butyl ester, which includes the steps of step one, subjecting 1-benzyl-4-piperidone and sodium borohydride to hydrogenation reduction reaction to obtain an intermediate A; step two, subjecting the intermediate A obtained in step one to catalysis debenzylation with palladium carbon to obtain an intermediate B; step three, reacting the intermediate B obtained in step two with di-tert-butyl dicarbonate in triethylamine alkaline solution to obtain an intermediate C; and step four, subjecting the intermediate C obtained in step three and toluene sulfonyl chloride to condensation reaction to obtain the 4-(toluene-4-Sulfonyl oxygen) piperidine-1- carboxylic tert-butyl ester. The synthesis method has the advantages that the operation reaction of the technical scheme provided is simple and convenient, no special condition reaction is needed, the method is close to actual production conditions of factories, as is proved by small experiment, the reaction repeatability is good, and the 4-(toluene-4-Sulfonyl oxygen) piperidine-1- carboxylic tert-butyl ester is suitable for factories to increase production; post-processing is simple and efficient, the production security coefficient is improved greatly, no apparent toxic substance is produced during the production process, the reaction condition is mild, and the safety is convenient to control during the production increase process.
Description
technical field [0001] The invention relates to a compound synthesis method, in particular to a synthesis method of 4-(toluene-4-sulfonyloxy)piperidine-1-carboxylic acid tert-butyl ester. Background technique [0002] 4-(toluene-4-sulfonyloxy)piperidine-1-carboxylate tert-butyl ester is a widely used compound, its molecular formula is [0003] . [0004] English name: 4-(Toluene-4-sulfonyloxy)piperidine-1-carboxylic acid tert-butyl ester [0005] Application 1: Vascular Adhesion Protein Antibody, [0006] Use 2: It is an intermediate in the synthesis of phosphodiesterase 4 (PDE4) inhibitors. Phosphodiesterase 4 has broad application prospects in COPD (chronic obstructive pulmonary disease), heart failure, asthma, impotence and other diseases, [0007] Use 3: It is an intermediate in the synthesis of H-PGDS inhibitors. H-PGDS inhibitors can be used for prostaglandin D2, [0008] Use 4: Used for the synthesis of quinoline derivatives (such as: DNA methylation regulator...
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IPC IPC(8): C07D211/46
Inventor 张正萍
Owner LANZHOU WANHAO BIOLOGICAL TECH