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Method for preparing oxycodone

A technology of dehydroxylation and methylpyridone is applied in the field of preparation of oxynidone, which can solve the problems of easy formation of highly toxic gas, complicated operation, complicated sewage and waste treatment and the like

Active Publication Date: 2010-06-09
BEIJING CONTINENT PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Chinese patent (CN2003000968) discloses a kind of synthetic method of formula I compound, with 2-amino-5 picoline as starting material, this method uses Me as phenolic hydroxyl protecting group, and the used reagent price of its deprotection is expensive, reaction It is easy to form highly toxic gas in the process, and the sewage waste treatment is cumbersome, the operation is cumbersome, and the yield is low (40%)

Method used

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  • Method for preparing oxycodone
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  • Method for preparing oxycodone

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preparation example Construction

[0038] The preparation method of the compound of formula I provided by the present invention is to mix 5-methylpyridone (compound of formula 4, or compound 4) and compound of formula II to obtain compound of formula III, and then react with dehydroxylation protection reagent to obtain formula I Compound:

[0039]

[0040] Wherein the R of formula II compound is an ether group, is selected from benzyl ether (-OCH 2 C 6 h 5 ), cyclohexyl ether tert-butyl ether (-OC(CH 3 ) 3 ), 4-picolyl ether or tetrahydropyranyl ether (-OTHP or

[0041] 5-picoline and formula II compound reaction obtains formula III compound, can carry out under the condition of this area routine, in a preferred example of the present invention is in dimethylformamide (DMF), anhydrous potassium carbonate and in the presence of cuprous iodide:

[0042]

[0043] In the present invention, according to the difference of R in the compound of formula III, in the step of obtaining the compound of for...

preparation example 1

[0072]

[0073] In 15mL of DMF, add 5g of 5-methylpyridone (compound 4), 17.7g of p-bromobenzenetetrahydropyranyl ether (compound 2, purchased from Sigma), 7.6g of anhydrous K 2 CO 3 , 1.06g CuI, the mixture was heated to 140 degrees, and the reaction was stirred for 5 hours. The completion of the reaction was monitored by TCL, cooled to room temperature, and filtered. The filter residue was washed with DMF, the filtrates were combined, and the solid was discarded. DMF was distilled off under reduced pressure, the residue was dissolved in ethyl acetate, washed with water, and then washed with saturated brine, the organic phase was dried over anhydrous sodium sulfate, concentrated, and dried to obtain an off-white to light gray solid, that is, compound 5 (9.7 g, recovered rate of 74%).

[0074] 5 g of compound 5 was dissolved in 30 mL of ethanol, and 0.05 g of p-toluenesulfonic acid was added. Stir at room temperature for about 1 hour. TLC showed that the reaction was c...

preparation example 2

[0077]

[0078] Compound 7 (yield 69%) was prepared by basically the same method as in Example 1, except that p-bromobenzenetetrahydropyranyl ether (compound 2) was replaced by bromophenylbenzyl ether (compound 6).

[0079] 5 g of compound 7 was dissolved in 30 mL of tetrahydrofuran, hydrogen gas was introduced, and 0.5 g of 10% Pd / C was added. Stir at room temperature for about 5 hours. TLC showed that the reaction was complete, filtered, and the filtrate was concentrated. 15 ml of ethanol was added to the residue, recrystallized, and filtered to obtain the compound of formula I (2.7 g, 78%).

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Abstract

The invention discloses a method for preparing a compound shown in a formula I. The method comprises the following steps: (1) mixing 5-methylpyridone and a compound shown in a formula II to obtain a compound shown in a formula III; and (2) reacting the compound shown in the formula III and a dehydroxylation protection reagent to obtain the compound shown in the formula I, wherein R is ether group.

Description

technical field [0001] The invention relates to the field of pharmacy, in particular to a preparation method of oxynidone. Background technique [0002] Liver fibrosis is the common pathological basis in the progress of chronic liver diseases. Various chronic injuries cause liver cell degeneration and necrosis, abnormal proliferation and excessive deposition of fibrous connective tissue, wrapping regenerated liver cells, forming "pseudolobules" and destroying the original liver tissue In the end, the liver will become nodular and harden, and the liver function will be damaged or even disappear completely, forming cirrhosis. Nearly one million people die from liver cirrhosis every year in the world, and it is still on the rise. In Europe, America, Japan, and China, liver cirrhosis is one of the leading causes of death, second only to cerebrovascular accidents, cardiovascular diseases, and malignant tumors . [0003] A variety of chronic diseases can cause liver fibrosis, su...

Claims

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Application Information

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IPC IPC(8): C07D213/64A61P1/16
Inventor 吴骏罗楹田彦伟金锐
Owner BEIJING CONTINENT PHARM CO LTD
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