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Alpha, alpha-dideuterated alcohol compound and preparation method thereof

An amide compound and compound technology, which is applied in the field of reductive deuteration of novel amide organic compounds, can solve the problems of low deuteration rate and poor regioselectivity, and achieve the effects of high deuteration rate, high selectivity and wide application range.

Pending Publication Date: 2021-04-20
北京奇点势能科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to overcome the existing α,α -The problem of using expensive flammable metal deuterides or low deuteration rate and poor regioselectivity in the preparation and synthesis method of dideuteroalcohol compounds, the present invention will conform to the general formula (1 ) of amide organic compounds reacted with divalent lanthanide transition metal compounds, Lewis bases and deuterium donor reagents in organic solvents to synthesize compounds conforming to the general formula (2) α,α -Dideuterated alcohols

Method used

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  • Alpha, alpha-dideuterated alcohol compound and preparation method thereof
  • Alpha, alpha-dideuterated alcohol compound and preparation method thereof
  • Alpha, alpha-dideuterated alcohol compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045]

[0046] To a 50 mL single-necked round-bottom flask under argon protection, add samarium diiodide-containing tetrahydrofuran solution (0.40 mmol, 0.1 mol / L), triethylamine (3.6 mmol), heavy water (3.6 mmol) in sequence, and compound 1a (0.1 mmol). The reaction mixture was stirred vigorously for 15 min at room temperature. Air was then bubbled in to quench the reaction. Dichloromethane and saturated sodium hydroxide solution were added for extraction, and the organic phase was dried and concentrated to obtain the target compound 2a with a yield of 90% and a deuterated rate of 96.0%.

[0047] The target product 2a obtained by the above synthesis method was detected by proton nuclear magnetic resonance spectrum and carbon spectrum, and the test results are as follows: 1 H NMR (400 MHz, CDCl3 ) δ 0.91 (t, J = 7.3 Hz, 3H), 1.24-1.43 (m, 15H), 1.56 (t, J = 7.3 Hz, 2H), 1.67 (br, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 14.3, 22.9, 25.9, 29.5, 29.6, 29.9, 29.8, 32.0, 32.9,...

Embodiment 2

[0049]

[0050] To a 50 mL single-necked round-bottom flask under argon protection, add samarium dichloride-containing n-pentane solution (0.50 mmol, 0.1 mol / L), pyrrolidine (7.2 mmol), deuterated ethanol (7.2 mmol), and compound 1a (0.1 mmol). The reaction mixture was stirred vigorously for 45 min at room temperature. Air was then bubbled in to quench the reaction. Dichloromethane and saturated sodium hydroxide solution were added for extraction, and the organic phase was dried and concentrated to obtain the target compound 2a with a yield of 95% and a deuterated rate of 93.0%.

[0051] The target product 2a obtained by the above synthesis method was detected by proton nuclear magnetic resonance spectrum and carbon spectrum, and the test results were the same as those in Example 1.

Embodiment 3

[0053]

[0054] To a 50 mL single-necked round-bottomed flask under argon protection, add samarium diiodide-containing tetrahydrofuran solution (0.80 mmol, 0.1 mol / L), triethylamine (7.2 mmol), heavy water (7.2 mmol) in sequence, and compound 1b (0.1 mmol). The reaction mixture was stirred vigorously for 60 min at room temperature. Air was then bubbled in to quench the reaction. Dichloromethane and saturated sodium hydroxide solution were added for extraction, and the organic phase was dried and concentrated to obtain the target compound 2b with a yield of 94% and a deuterated rate of 95%.

[0055] The target product 2b obtained by the above synthesis method was detected by proton nuclear magnetic resonance spectrum and carbon spectrum, and the test results are as follows: 1 H NMR (400 MHz, CDCl 3 ) δ 0.92 (t, J = 7.0 Hz, 3 H), 1.25-1.44 (m, 15 H), 1.59 (t, J = 7.0 Hz, 2 H), 1.69 (br, 1 H); 13 C NMR (100 MHz, CDCl 3 ) δ 13.9, 22.4, 25.5, 29.0, 29.1, 29.3, 29.2, 31.7,...

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Abstract

The invention relates to a method for synthesizing an alpha, alpha-dideuterated alcohol compound shown in a general formula (2), which is characterized in that an amide compound shown in a general formula (1) reacts with a bivalent lanthanide transition metal compound, a deuterium donor reagent and Lewis base in an organic solvent I to generate the alpha, alpha-dideuterated alcohol compound shown in the general formula (2) . compared with the traditional method, the method has the advantages of strong selectivity, high yield, high deuteration rate, few toxic and side products, low cost, mild reaction conditions, simplicity in operation, environmental friendliness and the like.

Description

technical field [0001] The invention belongs to the field of organic synthesis and relates to α,α -Di-deuterated alcohol compounds and their use in synthesis α,α -A method for the reduction deuteration of a novel amide organic substance of a dideuterioalcohol compound. Background technique [0002] There are more and more applications of deuterated compounds in biopharmaceuticals, new materials, metabolomics research, analytical chemistry, etc. ( Angew. Chemie Int. Ed. 2018, 57 (7), 1758–1784.). For example, in food safety testing, deuterated compounds play an important role. By selecting a suitable deuterated compound as an internal standard, the amount of nutrients and harmful substances in food can be accurately quantified, providing data for the formulation of food safety testing standards support. In addition, in drug reaction mechanism and toxicology research, deuterated compounds will also be widely used. In cell experiments and animal experiments for the develo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/147C07C31/125C07C33/20C07C33/14C07C33/26C07C33/025C07C41/26C07C43/23C07C319/20C07C323/19C07C213/08C07C215/68C07D209/12C07B41/02
Inventor 刘伟茜钟霞
Owner 北京奇点势能科技有限公司
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