反应详情

温度

0 °C

3-(4-fluorophenyl)-1-(2-methyl-2-phenylhydrazinyl)hex-5-en-3-ol (14 mg, 0.04 mmol) and triethylamine (3 drops) was dissolved in toluene (1 mL). The solution was cooled to 0° C. and phosgene (3 drops, 20% toluene solution) was added. After 1 h, more phosgene was added (3 drops, 20% toluene solution) and the reaction was allowed to warm to rt overnight. The solvent was evaporated and the residue was redissolved in toluene. DBU (5 drops) was added and the solution heated to reflux for 4 h. The solvent was evaporated and the residue was purified by preparative HPLC to afford 6-allyl-6-(4-fluorophenyl)-3-(methyl(phenyl)amino)-1,3-oxazinan-2-one (8.8 mg). LC-MS Method 1 m/z=341 (M+1). 1H NMR (CDCl3) δ 7.43-7.37 (br m), 7.25-7.26 (m), 7.19-7.12 (m), 6.99 (t), 6.85 (m), 6.72-6.66 (m), 6.07 (d), 6.73 (m), 5.15-5.05 (m), 3.42 (m), 3.33 (m), 3.14 (s), 2.85 (s), 2.65-2.55 (m), 2.50-2.34 (m).

1. temperatureto warm to rt overnight
2. customThe solvent was evaporated
3. dissolutionthe residue was redissolved in toluene
4. additionDBU (5 drops) was added
5. temperaturethe solution heated
6. temperatureto reflux for 4 h
7. customThe solvent was evaporated
8. customthe residue was purified by preparative HPLC