The preparation method of (1s,2r)-2-phenylcyclohexanol

A technology of phenylcyclohexanol and epoxycyclohexane, applied in the field of chiral alcohol synthesis, can solve problems such as hindered mass production, achieve the effects of high ee value and purity, good prospects for enlarged production, and outstanding substantive characteristics

Active Publication Date: 2022-06-24
ZHENGZHOU INST OF CHIRAL DRUGS RES CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few research reports on how to synthesize and resolve (1S,2R)-2-phenylcyclohexanol at home and abroad, which hinders its mass production.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] The present embodiment provides a preparation method of (1S,2R)-2-phenylcyclohexanol, and the specific steps include:

[0016] Dissolve 4.9g of epoxycyclohexane in tetrahydrofuran in the solvent, maintain the temperature at -10°C, then add 0.5g of cuprous chloride to the system, stir evenly, and add 14.5g of phenylmagnesium bromide dropwise to the reaction system tetrahydrofuran solution;

[0017] After the dropwise addition was completed, the reaction was performed for 3 hours. After the reaction was completed, saturated aqueous ammonium chloride solution was added at 10 °C for quenching treatment, and then the upper organic layer was collected. After concentration, the crude product was obtained. The crude product was distilled and recrystallized to obtain 7.5 g the racemate of chiral 2-phenylcyclohexanol;

[0018] 7.5g of the racemate of the chiral 2-phenylcyclohexanol, 7.7g of D-dibenzoyltartaric acid and n-hexane were sequentially added to the reaction vessel; sti...

Embodiment 2

[0023] The present embodiment provides a preparation method of (1S,2R)-2-phenylcyclohexanol, and the specific steps include:

[0024] Dissolve 4.9g of epoxycyclohexane in 2-methyltetrahydrofuran in the solvent, maintain the temperature at -10°C, then add 0.7g of cuprous bromide to the system, stir evenly, and add 15.3g dropwise to the reaction system Tetrahydrofuran solution of phenylmagnesium bromide;

[0025] After the dropwise addition was completed, the reaction was performed for 2 hours. After the reaction was completed, saturated aqueous ammonium sulfate solution was added at 20°C for quenching treatment, and then the upper organic layer was collected. After concentration, the crude product was obtained. The crude product was distilled and recrystallized to obtain 7.9 g the racemate of chiral 2-phenylcyclohexanol;

[0026] 7.9g of the racemate of the chiral 2-phenylcyclohexanol, 8.1g of resolving agent (6.5g of D-dibenzoyltartaric acid, 1.6g of water) and n-hexane were ...

Embodiment 3

[0029] The present embodiment provides a preparation method of (1S,2R)-2-phenylcyclohexanol, and the specific steps include:

[0030] Dissolve 5.1g of epoxycyclohexane in tetrahydrofuran in the solvent, maintain the temperature at -10°C, then add 0.71g of cuprous chloride to the system, stir evenly, and add 15.4g of phenylmagnesium bromide dropwise to the reaction system tetrahydrofuran solution;

[0031] After the dropwise addition was completed, the reaction was performed for 3 hours. After the reaction was completed, saturated aqueous ammonium chloride solution was added at 15°C for quenching treatment, then the upper organic layer was collected and concentrated to obtain the crude product. The crude product was distilled and recrystallized to obtain 8.3 g the racemate of chiral 2-phenylcyclohexanol;

[0032] Add 8.3 g of the chiral 2-phenylcyclohexanol racemate, 8.2 g of D-dibenzoyl tartaric acid and n-hexane in sequence into the reaction vessel; stir at 60 ° C for 4 h, a...

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PUM

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Abstract

The invention provides a method for preparing (1S,2R)-2-phenylcyclohexanol, which specifically comprises the steps of mixing epoxycyclohexane solution, tetrahydrofuran solution of phenylmagnesium bromide, cuprous chloride or cuprous bromide Perform a mixed reaction for 1h to 3h, then quench with saturated ammonium chloride or saturated ammonium sulfate aqueous solution; collect the upper organic layer and conduct concentration, distillation, and recrystallization to obtain the racemic solution of chiral 2-phenylcyclohexanol The chiral 2-phenylcyclohexanol racemate is resolved to obtain (1S,2R)-2-phenylcyclohexanol. The method can make the ee value of the obtained product reach more than 98%, the process is simple, and the product has high purity.

Description

technical field [0001] The invention relates to the technical field of chiral alcohol synthesis, in particular to a preparation method of (1S,2R)-2-phenylcyclohexanol. Background technique [0002] Chiral alcohols are an important class of alcohol compounds, which widely exist in drugs, pesticides, food, synthetic intermediates, natural products and biologically active compounds, especially in the field of chiral drugs. The enantiomers of chiral drugs have very similar physical properties, however, they are metabolized, transformed or activated in different ways within the organism, resulting in very different pharmacological effects, thus obtaining high enantioselectivity or high diastereoselectivity. A single isomer is significant. And (1S,2R)-2-phenylcyclohexanol is a kind of chiral alcohol, and it is the key intermediate of various chiral drugs. split. And the existing racemate resolution method usually includes the method of adopting acid-base treatment and then carr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C29/36C07C29/74C07C29/88C07C35/21
CPCC07C29/36C07C29/74C07C29/88C07B2200/07C07C2601/14C07C35/21
Inventor 邓照西
Owner ZHENGZHOU INST OF CHIRAL DRUGS RES CO LTD
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