A large amount of preparation method of chiral sulfinamide monophosphine ligand

A technology for sulfenamide mono- and phosphine ligands, which is applied in the directions of organic chemistry methods, chemical instruments and methods, and compounds of Group 5/15 elements of the periodic table, etc. and other problems to achieve the effect of improving the synthesis efficiency

Active Publication Date: 2021-10-15
苏州凯若利新材料科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The synthesis route of the ligand is simple, but the purification of the ligand is obtained by column chromatography, which uses more organic solvents and is not conducive to the promotion of the technological production of the ligand.

Method used

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  • A large amount of preparation method of chiral sulfinamide monophosphine ligand
  • A large amount of preparation method of chiral sulfinamide monophosphine ligand
  • A large amount of preparation method of chiral sulfinamide monophosphine ligand

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Example 1: Large-scale synthesis of chiral sulfinimides

[0025]

[0026] Wherein, THF is tetrahydrofuran; N 2 is nitrogen; Ti(O i Pr) 4 For tetraisopropyl titanate.

[0027] Accurately weigh o-diphenylphosphinebenzaldehyde (52.5mmol) and R-(+)-tert-butylsulfinamide (57.75mmol) in a 500mL three-necked reaction flask, and add 250mL of dry Tetrahydrofuran. Placed at 50° C. for 20 h. After the solvent temperature stabilized, tetraisopropyl titanate (157.5 mmol) was added dropwise through a constant-pressure low-liquid funnel as a condensation agent. After the complete reaction of the raw materials was detected by TLC, 100 mL of ethyl acetate was added to the reaction flask to dilute the solution. Then transfer the reaction solution to a 2L beaker filled with 200mL of saturated saline, and stir it rapidly with a glass rod for 5min to fully hydrolyze the tetraisopropyl titanate, and use a sand core funnel covered with diatomaceous earth to pump Filter, and wash the ...

Embodiment 2

[0029] Embodiment 2: the synthesis of chiral sulfinamide monophosphine ligand

[0030]

[0031] Add imine (40mmol) into a dry 500mL three-necked reaction flask, add 250mL of redistilled tetrahydrofuran under nitrogen atmosphere, and place it at -48°C. After the solution temperature is completely stable, add 80mL of phenyl bromide The magnesium reagent was placed in a constant pressure funnel (80.0 mmol), and the rate of addition was controlled to 2 drops per second. After reacting for 2 hours, turn off the refrigeration and stir overnight, and then continue to stir at room temperature for 2 hours. After the reaction was detected by TLC, 100 mL of saturated ammonium chloride solution was added to quench the reaction. Transfer to a 1L separatory funnel, extract three times with 100mL ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, and concentrate. The crude product was dissolved in 56 mL of acetone, then 40 mL of distilled water was added dropw...

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Abstract

The invention discloses a mass preparation method of a chiral sulfinamide monophosphine ligand. The chiral sulfinamide and 2-phenylphosphine benzaldehyde are used as raw materials to condense to obtain an intermediate chiral sulfenimide. Then it undergoes nucleophilic addition reaction with phenylmagnesium bromide reagent to generate chiral sulfinamide monophosphine ligand. Both the intermediate imine product and the final chiral sulfinamide monophosphine ligand are purified by crystallization without column chromatography. The method has the characteristics of cheap and easy-to-obtain raw materials, simple synthesis steps, large-scale synthesis and preparation, and a product with a specific three-dimensional structure. The method has mild conditions and is of great significance for the future technological and commercial development of chiral sulfinamide monophosphine ligand products.

Description

technical field [0001] The invention relates to a method for mass preparation of chiral sulfinamide monophosphine ligands, and belongs to the technical field of chemical substances and their synthesis. Background technique [0002] Each configurational isomer of a chiral compound usually exhibits different biological and catalytic activities. Therefore, it is very important to obtain a single chiral configuration isomer compound in organic synthesis. The method of asymmetric catalytic synthesis is currently one of the most effective methods to obtain single chiral isomer compounds. Using a small amount of chiral ligands as catalysts can efficiently and specifically prepare a large number of chiral compounds. It not only reduces the generation of by-product isomers, greatly improves the utilization rate of raw material atoms, but also reduces the pollution to the environment, which is in line with the current concept of green chemistry advocated. In asymmetric synthesis, c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/50
CPCC07B2200/07C07F9/5022C07F9/5054C07F9/5095
Inventor 肖元晶胡岸靖张展鸣张俊良
Owner 苏州凯若利新材料科技有限公司
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