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The preparation method of 3-hydroxyl oxetane compounds

A technology of hydroxyoxetane and benzaldehyde, applied in organic chemistry, bulk chemical production, etc., can solve the problems of synthesis and industrial production limitations, expensive carbonates, etc.

Inactive Publication Date: 2016-02-17
南京菲兰化妆品有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The disclosed method is basically limited because the carbonates are too expensive for normal industrial use
[0016] Although oxetane compounds have good application prospects, their synthesis and industrial production are greatly restricted.

Method used

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  • The preparation method of 3-hydroxyl oxetane compounds
  • The preparation method of 3-hydroxyl oxetane compounds
  • The preparation method of 3-hydroxyl oxetane compounds

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Embodiment Construction

[0031] 1, Preparation of 3-hydroxyl-oxetane

[0032]

[0033] Synthesis of 1-2

[0034] Add glycerol (92.09g, 1.0mol), benzaldehyde (116.73g, 1.1eq) and a catalytic amount of p-toluenesulfonic acid (0.1eq) into a reaction flask equipped with a water separator, add 1000ml of toluene and stir the reflux fraction Water, stop the reaction when the amount of water is close to the theoretical amount, add 500ml of water solution, extract the water phase with 500ml of toluene twice, combine the organic phase, wash once with 1000ml saturated saline, dry and concentrate, the colorless liquid distilled under reduced pressure 1- 2166.7g, yield 92.5%. MS(ESI)m / z181.0[M+H] + .

[0035] Synthesis of 1-3

[0036] Dissolve 1-2 (150,00g, 832.41mmol) in 1000ml THF, keep the system temperature at 0-10 degrees, add 2.5M n-butyllithium (333.0ml, 1.0eq) dropwise, stir for 30min after dropping, and then Benzyl chloride (110.63g, 1.05eq) was added dropwise, allowed to rise to room temperature ...

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Abstract

The invention discloses a synthetic method of a 3-hydroxy oxetane compound shown as a formula I. The method provided by the invention employs substituted glycerol I-1 as a raw material, which is subjected to condensation with aldehydes and ketones compounds to obtain a compound I-2; the I-2 is subjected to R2 protection to obtain a compound I-3; the compound I-3 is subjected to removal of aldehydes and ketones protecting groups to obtain a compound I-4; the compound I-4 is subjected to intramolecular cyclization to obtain a compound I-5; and the compound I-5 is subjected to removal of R2 protection to obtain a target compound I. Although the method has a long route, the reaction conditions are mild, and the post treatment and detection are convenient; therefore, the method is suitable for industrialized production.

Description

technical field [0001] The invention belongs to the field of synthesis of pharmaceutical intermediates, and in particular relates to a preparation method of 3-hydroxyxetane compounds. Background technique [0002] Oxetane compounds are very important drug synthesis fragments in medicinal chemistry. They were first prepared by Reboul more than 130 years ago, but they are rarely used in medicinal chemistry. With the development of medicinal chemistry research, oxetane compounds are more and more popular among medicinal chemists. The molecular building blocks are contained in marketed drugs, natural products, and pesticides. They can not only Improve the solubility, fat solubility, and alkalinity of drug molecules, and can improve the metabolic stability of drug molecules. Therefore, using oxetane compounds as synthetic building blocks for drug molecule design, [0003] It has become an effective means to improve the properties of small molecule drug candidates. [0004] ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D305/08
CPCY02P20/55
Inventor 朱凯刘兆刚吴刚
Owner 南京菲兰化妆品有限公司