Binol → HCID 3013585, compound

Participants

Reaction Steps

To a solution of (S)-(−)-1,1′-bi-2-naphtol (87.5 mg) in toluene (10 ml) were added titanium tetraisopropoxide (45.2 μl) and water (55 μl) at room temperature and the mixture was stirred for 1 hour. To the reaction solution were added 7-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[4-(4-propyl-4H-1,2,4-triazol-3-ylmethylthio)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (1.0 g) and cummene hydroperoxide (80%, 0.31 ml) and the mixture was stirred for 20 hours at room temperature Cumene hydroperoxide (80%, 0.14 ml) was added to the mixture, and the mixture was further stirred for 10 hours. To the reaction solution was added an aqueous solution of sodium thiosulfate and the mixture was stirred for several minutes and extracted with ethyl acetate. The organic layer was washed with sodium bicarbonate solution and saturated brine, and dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was separated and purified by column chromatography (basic silica gel, ethyl acetate→ethanol:ethyl acetate 1:19), to give (−)-7-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[4-(4-propyl-4H-1,2,4-triazol-3-ylmethylsulfinyl)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (Compound 177) (860.9 mg) as yellow amorphous.

Provenance & Evidence