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Total-deuteration tert butyl alcohol preparation method

A deuterated tert-butanol and deuterated technology, which is applied in the field of organic synthesis, can solve the problem of no high-abundance per-deuterated tert-butanol synthesis method, is not suitable for large-scale preparation of per-deuterated tert-butanol, and has no practical value and other problems, to achieve the effect of improving the convenience of operation, improving the conversion rate and product yield, and mild reaction conditions

Active Publication Date: 2018-06-15
上海枢炬化工有限公司
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  • Description
  • Claims
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Problems solved by technology

[0005] In the prior art, although the synthetic method of deuterated tert-butanol can be seen, there is no synthetic method of high-abundance all-deuterated tert-butanol
And in the method for synthesizing deuterated tert-butanol of the prior art, the diethyl ether that has is adopted as reaction solvent, because the flash point of diethyl ether is low and has serious potential safety hazard, is therefore not suitable for large-scale preparation of all deuterated tert-butanol, and Some methods use tetrahydrofuran instead of diethyl ether as the reaction solvent, the yield of the reaction is very low, and it has no practical value at all.

Method used

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[0019] The inventors of the present application have unexpectedly found that when deuterium methylmagnesium iodide is used as the Grignard reagent and anhydrous manganese chloride is used as the catalyst, a very ideal yield can be obtained, and the obtained all-deuterated tert-butanol High abundance. For this reason, the present invention provides a kind of preparation method of full deuterium tert-butanol, it comprises the steps: make deuterium methylmagnesium iodide and deuterium acetone in anhydrous tetrahydrofuran, in the presence of anhydrous manganese chloride Carry out Grignard reaction, and then carry out hydrolysis to obtain all deuterated tert-butanol.

[0020] Concrete reaction process is as follows;

[0021]

Embodiment 1

[0025] This example provides a method for preparing all-deuterated tert-butanol, specifically: in a 2000mL three-necked flask equipped with a thermometer and a condenser tube, add 185g of deuteromethylmagnesium iodide, 1000mL of anhydrous tetrahydrofuran, and 8g of anhydrous chlorine Manganese chloride, then dropwise add 64g deuterated acetone, react at 10±2°C for 4-6 hours, then add heavy aqueous solution dissolved in deuterium chloride to the above-mentioned flask to quench the reaction, and obtain all deuterated tert-butanol The reaction solution, after rectification, can obtain the high-abundance perdeuterated tert-butanol product: 67g, the yield is 80%, the detection of the perdeuterated tert-butanol product, the GC purity is 99.9%, and the isotope abundance detected by mass spectrometry is 99.8 %(atom %D). Elemental analysis theoretical value: C 57.07%, D23.92%, O19.00%; measured value: C 57.05%, D23.91%, O19.02%.

Embodiment 2

[0027] This example provides a method for preparing all-deuterated tert-butanol, specifically: in a 2000mL three-necked flask equipped with a thermometer and a condenser tube, add 185g of deuteromethylmagnesium iodide, 1000mL of anhydrous tetrahydrofuran, and 8g of anhydrous chlorine Manganese chloride, then dropwise add 64g of deuterated acetone, react at -10±2°C for 4-6 hours, then add heavy aqueous solution dissolved in deuterated sulfuric acid to the above flask to quench the reaction, and obtain perdeuterated tert-butyl Alcohol reaction solution, through rectification, obtains the high-abundance per-deuterated tert-butanol product: 69g, yield 82%, detects the per-deuterated-tert-butanol product, GC purity is 99.9%, and the isotope abundance detected by mass spectrometry is 99.7% (atom% D). Elemental analysis theoretical value: C 57.07%, D23.92%, O19.00%; measured value: C 57.06%, D23.91%, O19.01%.

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Abstract

The invention discloses a total-deuteration tert butyl alcohol preparation method which comprises the following steps: firstly, making deuterium methyl magnesium iodide and deuteration acetone performGrignard reaction in anhydrous tetrahydrofuran under the existence of anhydrous manganese chloride; then hydrolyzing a reaction product under the acid condition to generate total-deuteration tert butyl alcohol, wherein the acid condition is formed by a heavy water solution which deuteration acid is added in. The total-deuteration tert butyl alcohol preparation method disclosed by the invention has the advantages of moderate reaction condition, high reaction yield, ability in obtaining abundant total-deuteration tert butyl alcohol and simpleness in technological operation.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of perdeuterated tert-butanol. Background technique [0002] Perdeuterated tert-butanol is an important chemical raw material and deuterated drug intermediate, and is a key starting material for the synthesis of deuterated atazanavir and other deuterated drugs. The structure of perdeuterated tert-butanol is as follows: [0003] [0004] Deuterated drugs are those in which one or more hydrogen elements in the drug are replaced with deuterium. Because deuterium and hydrogen differ only by one neutron in structure, they have similar physical and chemical properties compared with original drugs, and due to isotope effects, deuterated drugs have unique biological stability and curative effect. [0005] In the prior art, although the synthetic method of deuterated tert-butanol can be seen, there is no synthetic method of high-abundance all-deuterate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/09C07C31/12
CPCC07B2200/05C07C29/09C07F3/02C07C31/12
Inventor 刘世领李玉强翁贵萍
Owner 上海枢炬化工有限公司
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