Methanol → HCID 118157400, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, ethyl 8-hexylsulfamoyl-octanoate (No. 6804262; 818.3 mg, 2.44 mmol) was dissolved in toluene (11 mL), and the mixture was cooled to −78° C. While maintaining the temperature at −78° C., a diluted solution of diisobutylaluminum hydride (1.5 M solution in toluene, 1.95 mL, 2.93 mmol) in toluene (2.9 mL) was added dropwise over 25 minutes, and the mixture was stirred at −78° C. for 1.5 hours. The reaction was monitored by LCMS. To this reaction solution was, then, further added a diluted solution of diisobutylaluminum hydride (1.5 M solution in toluene, 0.81 mL, 1.22 mmol) in toluene (0.9 mL) was added dropwise over 10 minutes, and the mixture was stirred at −78° C. for 1 hour. Methanol (0.65 mL) was added to the reaction solution, which was stirred at −78° C. for 10 minutes to stop the reaction. A saturated aqueous solution (3.0 mL) of Rochelle salt and water (9.0 mL) were further added and the mixture was stirred at 0° C. for 1 hour. Insoluble material was filtered off and washed with dichloromethane. The filtrate was then extracted with dichloromethane. The organic layer was washed with water, and dried over anhydrous sodium sulfate, and then filtered. Dichloromethane was distilled off to obtain the target 8-oxo-octane-1-sulfonic acid hexyl amide (ESI (LC/MS positive mode) m/z 292 (M+H); Rt 1.68 min.).

Provenance & Evidence