Ammonium Chloride → HCID 58130330, compound

Participants

Reaction Conditions

Reaction Steps

The compound (1.0 mmol, 282 mg) obtained in (1) above and SeO2 (1.2 mmol, 133 mg) were dissolved in 5 mL of chlorobenzene, and the solution was refluxed for 12 hours under a nitrogen atmosphere. After the disappearance of the starting materials was confirmed by NMR, the temperature of the solution was returned to room temperature, and saturated NaHCO3 was poured thereinto to terminate the reaction. The organic substances were extracted with methylene chloride, the obtained organic layer was dried over magnesium sulfate, and the solvents were evaporated under reduced pressure. The residue was passed through a silica-gel column, and directly used in the subsequent reaction. The obtained mixture was dissolved in 2 mL of methanol, to which NaBH4 (1.0 mmol, 38 mg) was added; and under a nitrogen atmosphere, the resulting product was stirred at 0° C. for 2 hours. A saturated ammonium chloride solution was added thereto to terminate the reaction. Then, the organic layer extracted with ethyl acetate was dried over magnesium sulfate, and the solvents were evaporated under reduced pressure. The residue was purified by silica gel column chromatography and recrystallized with hexane/ethyl acetate. Thereby, the title compound (0.41 mmol, 122 mg) was obtained in a two-step yield of 41%.

Provenance & Evidence