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Process for synthesizing teprenone

A synthesis process, technology of teprenone, applied in the preparation of carbon-based compounds, hydroxyl compounds, organic compounds, etc.

Inactive Publication Date: 2016-07-06
四川墨凯科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The challenge now lies in the synthesis of the precursors for teprenone, namely (6E,10E)-geranyllinalool or 1-halo-3,7,11,15-tetramethyl-hexadeca-2,6 ,10,14-tetraene

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] (1) Synthesis of (2E,6E)-2,6,10-trimethyldodeca-2,6,11-triene-1,10-diol

[0018] Add 0.221 grams (0.002 moles) of selenium dioxide, 40 milliliters (0.36 moles) of 90% tert-butyl hydroperoxide, 35 milliliters of dichloromethane, and 19.75 grams (0.10 moles) of tertiary nerolidol into a round-bottomed flask at room temperature The reaction was stirred for 24 hours. Next, the reaction mixture was washed with sodium bisulfite and saturated brine. Then, it was extracted three times with dichloromethane, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure at 30 degrees Celsius under rotary rotation. 20 ml of methanol and 3.8 g of sodium borohydride were added to the obtained oil, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with 1 mol / liter of dilute sulfuric acid, extracted 3 times with ethyl acetate, the organic phase was dried over anhydrous sodium sulfate, filtered to r...

Embodiment 2

[0020] (2) Synthesis of (6E,10E)-3,7,11-trimethyl-12-(tetrahydro-2H-pyran-2-yloxy)dodeca-1,6,10-triene-3- alcohol

[0021] (2E,6E)-2,6,10-trimethyldodeca-2,6,11-triene-1,10-diol 2.12g (0.01mol), dihydropyran 1.09g (0.013mol) and 0.172 g (0.0001 mol) of p-toluenesulfonic acid were heated at 60°C for 5 hours. After cooling to room temperature, the reaction was quenched with aqueous sodium bicarbonate solution, extracted 3 times with ethyl acetate, the organic phase was dried over anhydrous sodium sulfate, the filter residue was removed by filtration, and the filtrate was concentrated under reduced pressure to obtain 2.36 grams of acetal (product rate of 93%).

Embodiment 3

[0023] (3) Synthesis of (6E,10E)-geranyllinalool

[0024] Add 1.61 g (0.005 mol) of acetal and 20 ml of anhydrous tetrahydrofuran into the round bottom flask, place the flask in an ice-water bath, then add 1.14 g (0.006 mol) of cuprous iodide, 2 mol / L iso 3 ml (0.006 mol) of pentenyl magnesium bromide, continue to stir for 6 hours, then quench with 2 mol / L dilute sulfuric acid, extract 3 times with ethyl acetate, wash the organic phase with water, dry over anhydrous magnesium sulfate, filter, The filtrate was concentrated under reduced pressure, and the obtained oil was separated and purified by silica gel column chromatography to obtain 0.74 g of (6E,10E)-geranyllinalool (yield 51%).

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PUM

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Abstract

The invention discloses a process for synthesizing teprenone.According to the process for synthesizing teprenone, nerolidol is adopted as an initial raw material and subjected to selenium dioxide and tert-butyl hydroperoxide oxidizing in sequence, nerolidol and dihydropyran are subjected to acid catalysis to form acetal, acetal reacts with a Grignard reagent on the presence of copper salt and reacts with methyl acetoacetate on the presence of aluminum salt, and the teprenone product consistent with the configuration of products sold on the market is obtained through four steps of reactions.According to a preparation method of teprenone, the raw material is cheap and easy to obtain, operation is easy and convenient, the reaction conditions are mild, and industrial production is expected to be achieved.

Description

technical field [0001] The invention relates to a synthesis process of teprenone, which belongs to the fields of medicine and fine chemical industry, and specifically relates to a process for synthesizing teprenone from tertiary nerolidol as a starting material. Background technique [0002] Teprenone (teprenone), the chemical name is 6,10,14,18-tetramethyl-5,9,13,17-nonadecatetraen-2-one, which is (5E,9E,13E) and (5Z,9E,13E) mixture of geometric isomers (3:2), colorless to pale yellow oily liquid with special aroma. [0003] Teprenone has strong anti-ulcer effect and improvement effect on gastric mucosal lesions for various experimental ulcers and gastric mucosal lesions. Synthesis and secretion, can promote the healing of gastric mucosal injury, can improve the biosynthesis of prostaglandins in gastric mucosa, improve gastric mucosal blood flow, suitable for the treatment of acute gastritis, gastric ulcer, etc. Teprenone is clinically used for the treatment of: 1. Acute ...

Claims

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Application Information

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IPC IPC(8): C07C45/00C07C49/203C07C29/00C07C31/125C07D309/12
CPCC07C45/00C07C29/00C07D309/12C07C49/203C07C31/125
Inventor 曾庆乐马昌周立宏
Owner 四川墨凯科技有限公司
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