Synthetic method of alpha-monodeuterated alcohol compound and deuterated drug
A synthesis method and compound technology, applied in the field of reductive deuteration of new aldehydes and ketones, can solve the problems of expensive ruthenium catalysts, poor chemoselectivity, and low deuteration rate of products, and achieve small dosage, good chemoselectivity, and deuterium The effect of high generation rate
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Embodiment 1
[0042]
[0043] Add dodiodis in a 25 mL single-mouth round bottom flask under argon protected (SMI) 2 The solution (0.100 mol / L) in tetrahydrofuran (0.100 mol / L) was 7.50 ml, and the compound 1a was 44.5 mg (0.300 mmol), and 150 mg (7.50 mmol) was overwater. The reaction mixture was stirred at room temperature for 15 min, followed by air to quench the reaction. Ethyl acetate was added to 1 M hydrochloric acid solution, and the organic phase was dried, concentrated, and the column chromatography was separated to obtain 44.5 mg of the target compound 2a, the yield was 98%, and the deuterated rate was 98%.
[0044] The target product 2a obtained by the above synthesis method is used to detect the nuclear magnetic resonance spectrum and carbon spectrum detection. The test results are as follows. 1 H NMR (300MHz, CDCL 3 Δ7.31-7.24 (m, 2H), 7.23-7.14 (m, 3H), 2.71 (m, 2H), 1.75 (M, 2H), 1.22 (BR, 1H), 1.22 (S, 3H); 13 C { 1 H} NMR (75MHz, CDCL 3 ) δ142.2, 128.5 (× 2), 125.9, 67.1 ...
Embodiment 2
[0046]
[0047] Add dodiodis in a 25 mL single-mouth round bottom flask under argon protected (SMI) 2 The solution (0.100 mol / L) in tetrahydrofuran (0.100 mol / L) was 7.50 mL, and the compound 1b was 48.7 mg (0.300 mmol), and 150 mg (7.50 mmol) was overwater. The reaction mixture was stirred at room temperature for 15 min, followed by air to quench the reaction. EtOAc.
[0048] The target product 2b obtained by the above synthesis method was used to detect the nuclear magnetic resonance spectrum and carbon spectrum detection, and the test results were as follows: 1 H NMR (300MHz, CDCL 3 Δ7.19-7.09 (m, 4H), 2.75 (D, J = 13.5 Hz, 1H), 2.67-2.58 (M, 3H), 1.57 (Br, 1H), 1.29-1.19 (m, 6H); 13 C { 1 H} NMR (75MHz, CDCL 3 ) δ142.5, 135.7, 129.4, 128.1, 68.5 (t, j C-D = 21.8Hz), 45.4, 28.5, 22.7, 15.6.
Embodiment 3
[0050]
[0051] Add dodiodis in a 25 mL single-mouth round bottom flask under argon protected (SMI) 2 The solution (0.100 mol / L) in tetrahydrofuran (0.100 mol / L) was 7.50 ml, and Compound 1C 63.1 mg (0.300 mmol) was 100 mg (7.50 mmol). The reaction mixture was stirred at room temperature for 15 min, followed by air to quench the reaction. EtOAc.
[0052] The target product 2c obtained by the above synthesis method is used to detect the nuclear magnetic resonance spectrum and carbon spectrum detection, and the test results are as follows: 1 H NMR (300MHz, CDCL 3 Δ7.41-7.14 (m, 10H), 3.79 (S, 1H), 1.69 (S, 1H), 1.17 (S, 3H); 13 C { 1 H} NMR (75MHz, CDCL 3 Δ142.6, 141.6, 128.9, 128.7, 128.7, 128.3, 126.9, 126.6, 69.7 (T, J C-D = 22.0 Hz), 60.6, 21.4.
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