Preparation method of tetrahydro-1,4-methylene benzo[d][1,2]oxazepine
A technology of methylene benzene and oxazepine, which is applied in the field of preparation of tetrahydro-1,4-methylenebenzo[d][1,2]oxazepine, can solve the problem of high reaction risk , low efficiency, difficult synthesis and other problems, to achieve the effect of easy substrate synthesis and convenient source
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[0019] Example 1:
[0020] Cp*Rh(OAc) 2 (7.0mg, 0.010mmol, 0.050equiv), AgOAc (80mg, 0.500mmol, 2.50equiv) were added to a 25mL sealed tube, and magnetons and 1mL solvent CF were added under nitrogen protection 3 CH 2 OH, after stirring for 10 minutes, nitrone 2 (0.200mmol, 1.00equiv) and methylenecyclopropane 3 (0.500mmol, 2.50equiv) were added to the sealed tube, and the reaction was stirred at 40°C for 24h, diatomaceous earth Filter and wash with 15 mL of ethyl acetate. The organic layer was spin-dried and directly subjected to column chromatography to obtain product 4, with a total yield of 84%. 1 H NMR, 13 The purity by C NMR was all greater than 95%.
[0021] 1 H NMR (400MHz, CDCl 3 )δ7.80(d, J=7.8Hz, 1H), 7.44(s, 4H), 7.29(s, 1H), 7.25(t, J=7.6Hz, 1H), 7.18(t, J=7.3Hz, 1H), 7.09(d, J=7.3Hz, 1H), 5.46(d, J=5.5Hz, 1H), 4.31(d, J=4.9Hz, 1H), 2.33(s, 1H), 2.02(t, J=10.2Hz,1H),1.35(s,9H),1.18(s,9H). 13 C NMR (101MHz, CDCl 3 )δ150.1, 142.4, 136.9, 134.0, 132.8, 129...
Example Embodiment
[0023] Example 2:
[0024] Cp*Rh(OAc) 2 (7.0mg, 0.010mmol, 0.050equiv), AgNO 2 (85mg, 0.500mmol, 2.50equiv) was added to a 25mL sealed tube, and magneton and 1mL solvent CF were added under nitrogen protection 3 CH 2 OH, after stirring for 10 minutes, nitrone 2 (0.200mmol, 1.00equiv) and methylenecyclopropane 3 (0.500mmol, 2.50equiv) were added to the sealed tube, and the reaction was stirred at 50°C for 24h, diatomaceous earth Filter and wash with 15 mL of ethyl acetate. The organic layer was spin-dried and directly carried out column chromatography to obtain product 4 with a total yield of 85%. 1 H NMR, 13 The purity by C NMR was all greater than 95%.
[0025] 1 H NMR (400MHz, CDCl 3 )δ7.80(d, J=7.8Hz, 1H), 7.44(s, 4H), 7.29(s, 1H), 7.25(t, J=7.6Hz, 1H), 7.18(t, J=7.3Hz, 1H), 7.09(d, J=7.3Hz, 1H), 5.46(d, J=5.5Hz, 1H), 4.31(d, J=4.9Hz, 1H), 2.33(s, 1H), 2.02(t, J=10.2Hz,1H),1.35(s,9H),1.18(s,9H). 13 C NMR (101MHz, CDCl 3 )δ150.1, 142.4, 136.9, 134.0, 132.8, 129.4...
Example Embodiment
[0027] Example 3:
[0028] Cp*Rh(OAc) 2 (7.0mg, 0.010mmol, 0.050equiv), Ag 2 CO 3 (55mg, 0.200mmol, 1.00equiv) was added to a 25mL sealed tube, and magneton and 1mL solvent CF were added under nitrogen protection 3 CH 2 OH, after stirring for 10 minutes, nitrone 2 (0.200mmol, 1.00equiv) and methylenecyclopropane 3 (0.500mmol, 2.50equiv) were added to the sealed tube, and the reaction was stirred at 30°C for 24h, diatomaceous earth Filter and wash with 15 mL of ethyl acetate. The organic layer was spin-dried and directly subjected to column chromatography to obtain product 4 with a total yield of 81%. 1 H NMR, 13 The purity by C NMR was all greater than 95%.
[0029] 1 H NMR (400MHz, CDCl 3 )δ7.80(d, J=7.8Hz, 1H), 7.44(s, 4H), 7.29(s, 1H), 7.25(t, J=7.6Hz, 1H), 7.18(t, J=7.3Hz, 1H), 7.09(d, J=7.3Hz, 1H), 5.46(d, J=5.5Hz, 1H), 4.31(d, J=4.9Hz, 1H), 2.33(s, 1H), 2.02(t, J=10.2Hz,1H),1.35(s,9H),1.18(s,9H). 13 C NMR (101MHz, CDCl 3 )δ150.1, 142.4, 136.9, 134.0, 132.8, ...
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