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.
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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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