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Preparation method of (R)-2-(2-methoxyphenyl)-2-(tetrahydropyran-4-oxy)-ethan-1-ol

A technology of methoxyphenyl and tetrahydropyran, applied in the field of medicine and biochemistry, can solve problems such as unreported compounds, and achieve the effects of avoiding splitting process, concise technical route and mild reaction conditions

Inactive Publication Date: 2020-10-09
SYNCOZYMES SHANGHAI
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

[0015] The asymmetric synthesis method of this compound has not been reported yet

Method used

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  • Preparation method of (R)-2-(2-methoxyphenyl)-2-(tetrahydropyran-4-oxy)-ethan-1-ol
  • Preparation method of (R)-2-(2-methoxyphenyl)-2-(tetrahydropyran-4-oxy)-ethan-1-ol
  • Preparation method of (R)-2-(2-methoxyphenyl)-2-(tetrahydropyran-4-oxy)-ethan-1-ol

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Embodiment 1

[0036] The preparation of embodiment 1 compound IV

[0037] Add 20g 2-methoxyacetophenone, 27g N-chlorosuccinimide, 1g p-toluenesulfonic acid into a 250mL reaction flask, add 160mL methanol, react at 35°C for 4h, concentrate after the reaction, and use dichloro Methane / water extraction, the organic layer was dried, filtered, and concentrated to obtain 18.3 g of chloride, with a yield of 74.43%. 1 For H NMR data see figure 1 .

Embodiment 2

[0038] The preparation of embodiment 2 compound IV

[0039] Add 20g 2-methoxyacetophenone, 30g N-bromosuccinimide, 1g p-toluenesulfonic acid into a 250mL reaction flask, add 160mL methanol, react at 35°C for 6h, concentrate after the reaction, and use dichloro Methane / water extraction, the organic layer was dried, filtered, and concentrated to obtain 19.5 g of bromide, with a yield of 65.1%.

Embodiment 3

[0040] The preparation of embodiment 3 compound IV

[0041] Add 20g 2-methoxyacetophenone, 30g N-iodosuccinimide, 1g p-toluenesulfonic acid into a 250mL reaction flask, add 160mL methanol, react at 35°C for 5h, concentrate after the reaction, and use dichloro Extracted with methane / water, the organic layer was dried, filtered and concentrated to obtain 22.6g of iodide with a yield of 61.5%.

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Abstract

The invention discloses a chemical-enzymatic preparation method of (R)-2-(2-methoxyphenyl)-2-(tetrahydropyran-4-oxy)-ethan-1-ol. The method includes subjecting a compound V as a raw material to a halogenating reaction to obtain a compound IV; then performing ketoreductase catalysis to obtain a compound III; reacting under an alkaline condition to obtain a compound II; and finally reacting with tetrahydropyran-4-ol to obtain a target product that is a compound I. The method adopts a chemical-enzymatic process for preparation, is concise in technical route and mild in reaction condition, avoidsthe use of toxic reagents with large danger coefficients, avoids a resolution process, is environment-friendly, is low in cost, and is suitable for industrial production.

Description

Technical field: [0001] The invention belongs to the field of medical biochemistry, in particular to a chemical-enzymatic method for (R)-2-(2-methoxyphenyl)-2-(tetrahydropyran-4-oxyl)ethan-1-ol Preparation. Background technique: [0002] Nonalcoholic steatohepatitis (NASH) is a chronic progressive liver disease caused by the accumulation of fat in the liver, which can lead to inflammation, liver fibrosis and cirrhosis. Acetyl-CoA carboxylase (ACC) is the rate-limiting enzyme in the process of fat de novo synthesis, and fat regeneration in NASH patients is significantly accelerated. Therefore, ACC inhibitors are very likely to reduce lipid synthesis or accelerate its breakdown. Since the number of NASH patients in China accounts for one-third of the global patients, there is a huge domestic market demand for the development of NASH therapies. [0003] GS-0976 is an acetyl-CoA carboxylase (ACC) inhibitor developed by Gilead Sciences for the treatment of nonalcoholic steatohe...

Claims

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Application Information

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IPC IPC(8): C07D309/12C07D303/22C12P7/22
CPCC07D309/12C07D303/22C12P7/22C07B2200/07
Inventor 竺伟徐俊杰袁利王波
Owner SYNCOZYMES SHANGHAI
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