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Synthesis method for N-Boc-3-piperidone

A technology of n-boc-3- and 1.n-boc-3-, which is applied in the field of pharmaceutical intermediate synthesis, can solve problems such as excessively long synthetic route of N-Boc-3-piperidone, and achieve short synthetic route. , the effect of reducing production costs and energy consumption, and reducing pollution

Inactive Publication Date: 2013-07-17
甘肃天骄商贸有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In order to overcome the problem that the synthesis route of N-Boc-3-piperidone is too long in the above-mentioned prior art, the present invention provides a new method for synthesizing N-Boc-3-piperidone

Method used

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  • Synthesis method for N-Boc-3-piperidone
  • Synthesis method for N-Boc-3-piperidone
  • Synthesis method for N-Boc-3-piperidone

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Experimental program
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Embodiment 1

[0027] first step:

[0028]

[0029] Dissolve 95 g of 3-hydroxypyridine (1.0 mol) in 500 ml of ethanol, cool the reaction solution below 5°C, add 180 g of benzyl bromide (1.05 mol) dropwise, drop it in half an hour, then return to room temperature and stir overnight . The completion of the reaction was monitored by TLC, filtered directly, and the filter cake was washed three times with 50 ml of ethanol, and then dried to obtain N-benzyl-3-hydroxypyridine quaternary ammonium salt (240 g, 0.90 mol), with a yield of 90%.

[0030] Step two:

[0031]

[0032] Dissolve 266 grams of N-benzyl-3-hydroxypyridine quaternary ammonium salt (1.0mol) in 1500 milliliters of ethanol, cool down to about 0°C in an ice-salt bath, slowly add 80 grams of sodium borohydride (2.11mol), when adding Keep the temperature at 0°C all the time. After the addition, the reaction solution returns to room temperature and reacts overnight. TLC monitors that the reaction is complete, add 100 milliliters...

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Abstract

The invention discloses a synthesis method for N-Boc-3-piperidone. The synthesis method comprises the following steps of: reacting 3-hydroxyl pyridine with benzyl bromide in an organic solvent to obtain an N-benzyl-3-hydroxyl pyridine quaternary ammonium salt; reducing the N-benzyl-3-hydroxyl pyridine quaternary ammonium salt by sodium borohydride to obtain N-benzyl-3-hydroxyl piperidine; reacting N-benzyl-3-hydroxyl piperidine with di-tert-butyl dicarbonate ester to obtain N-Boc-3-hydroxyl piperidine under hydrogen protection and the catalysis of a palladium-carbon catalyst; and reacting N-Boc-3-hydroxyl piperidine with the mixed oxidant of dimethyl sulfoxide and oxalyl chloride to obtain N-Boc-3-piperidone under the action of an organic base. Compared with the existing synthesis method, the synthesis method disclosed by the invention is shorter in synthesis route, and easier for separation and purification of reactants, thus reducing the production cost, the energy consumption and the pollution; and the total productivity of N-Boc-3-piperidone can achieve more than 42%, and the purity thereof is greater than 98%.

Description

technical field [0001] The invention belongs to the field of synthesis of pharmaceutical intermediates, in particular to a new synthesis method of N-Boc-3-piperidone. Background technique [0002] N-Boc-3-piperidone is a very important intermediate of medicine, pesticide and other chemical additives. At present, the domestic synthesis process of N-Boc-3-piperidone is based on γ-butyrolactone as raw material, and undergoes six steps of benzylaminolysis, hydrolysis, esterification, condensation with ethyl bromoacetate, cyclization, and hydrolysis decarboxylation. Generate 1-benzyl-3-piperidone hydrochloride, and then debenzylate Boc to obtain N-Boc-3-piperidone, because the above-mentioned process steps are longer, the raw material cost is high, and the energy consumption is high, and the product Efficiency is low again, and the purity of the synthetic N-Boc-3-piperidone is also lower, and pollution is more serious, is unfavorable for industrialized production. Contents of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/74
Inventor 王思峰
Owner 甘肃天骄商贸有限公司
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