Novel method for synthesizing isotopic hydroxyl and methylsulfonyl methyl compound

A technology of methanesulfonylmethyl and iso-hydroxyl, which is applied in the field of organic compound synthesis, can solve the problems of unfavorable environmental protection of waste liquid, poor stability of intermediates, low conversion rate and yield, and achieve short steps, mild reaction conditions, The effect of lowering the security level

Inactive Publication Date: 2020-05-29
CHENGDU CHEMPARTNER
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The technical problem to be solved by the present invention is that in the prior art, there are many steps, many side reactions, poor stability of intermediates, easy ring openin

Method used

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  • Novel method for synthesizing isotopic hydroxyl and methylsulfonyl methyl compound
  • Novel method for synthesizing isotopic hydroxyl and methylsulfonyl methyl compound
  • Novel method for synthesizing isotopic hydroxyl and methylsulfonyl methyl compound

Examples

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Effect test

Embodiment 1

[0048] Example 1. Preparation of 8-(methylsulfonylmethyl)-1,4-dioxospiro[4,5]decane-8-ol

[0049]

[0050] Add 0.5g of dimethyl sulfone and 6mL of tetrahydrofuran to the reaction vessel, replace the reaction system with argon and then stir and cool to -70℃, add 1.4mL of n-butyllithium with a concentration of 2.5mol / L and keep the temperature at -70℃ Stir for 0.5 hours; then add 0.4 g of 1,4-cyclohexanedione monoethylene ketal (S-1) in tetrahydrofuran (6 mL) into the reaction system, keep the temperature of the reaction solution at -70°C and stir for 2 hours, Warm to room temperature and stir for 2 hours; the reaction solution is extracted with saturated aqueous ammonium chloride solution, extracted with ethyl acetate, the combined organic phases are washed with saturated brine, dried with anhydrous sodium sulfate, filtered, and the filtrate is spin-dried at low temperature to remove the solvent and residue Column chromatography was separated and purified to obtain the off-white s...

Embodiment 2

[0054] Example 2. Preparation of 5-hydroxy-5-(methylsulfonylmethyl)hexahydropentene-2(1H)-one

[0055]

[0056] Add 0.5 g of dimethyl sulfone and 6 mL of tetrahydrofuran to the reaction vessel, replace the reaction system with argon, stir and cool to -75°C, add 1.4 mL of n-butyl lithium with a concentration of 2.5mol / L, and keep the temperature at -75°C Stir for 0.5 hours; then add 0.5g of bicyclo[3.3.0]octane-3,7-dione (S-2) in tetrahydrofuran (7mL) solution into the reaction system, keep the temperature of the reaction solution at -75℃ and stir for 2 hours , Warmed to room temperature and stirred for 3 hours; the reaction solution was extracted with a saturated aqueous solution of ammonium chloride, extracted with ethyl acetate, the combined organic phases were washed with saturated brine, dried with anhydrous sodium sulfate, filtered, and the filtrate was spin-dried at low temperature to remove the solvent. The residue was separated and purified by column chromatography to obt...

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Abstract

The invention provides a novel method for synthesizing an isotopic hydroxyl and methylsulfonyl methyl compound. The method comprises the following steps: carrying out low-temperature lithiation reaction on a keto-carbonyl raw material compound and dimethyl sulfone, and carrying out one-step synthesis to obtain an isotopic hydroxyl and methylsulfonyl methyl series compound in situ on keto-carbonyl.According to the novel preparation method of the isotopic hydroxyl and methylsulfonyl methyl compound, the whole synthesis route is short in step, good in repeatability, wide in application substrate, high in yield, mild in operation condition and high in safety, and large-scale production and industrial popularization and application are facilitated.

Description

Technical field [0001] The present invention relates to the technical field of organic compound synthesis, and more specifically, to a new method for synthesizing iso-hydroxyl and methylsulfonyl methyl groups. Background technique [0002] The ketone carbonyl group generates in-situ iso-hydroxyl and methylsulfonylmethyl series compounds, which are an important intermediate compound. The hydroxyl and methylsulfonylmethyl functional groups play a very important role in the oil-water partition properties of the chemical molecular structure. An important intermediate compound for a variety of pharmaceutical compounds. [0003] At present, in the existing published literature, the method for generating iso-hydroxyl and methylsulfonyl methyl series compounds in situ in the ketone carbonyl group is to first perform the epoxy reaction of the ketone carbonyl group, and then conduct the ring-opening reaction in the presence of sodium methyl mercaptan to obtain the iso-hydroxyl group. And di...

Claims

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Application Information

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IPC IPC(8): C07D317/72C07C315/00C07C317/24
CPCC07D317/72C07C315/00C07C317/24
Inventor 仵清春鲍龙姜志成范文坤
Owner CHENGDU CHEMPARTNER
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