Water → HCID 69202020, compound

Participants

Reaction Steps

A 2 mol/L solution of borane dimethylsulfide complex in tetrahydrofuran (1.96 mL) was added dropwise to a solution of 2-(4-bromophenoxy)-N—((R)-2-hydroxy-2-{3-[methanesulfonyl-(2-trimethylsilylethoxymethyl)amino]-4-(2-trimethylsilylethoxymethoxy)phenyl}ethyl)acetamide (1.35 g) in tetrahydrofuran (10 mL) at room temperature under an atmosphere of argon. The mixture was stirred under ref lux for 1.5 hrs, and then cooled to room temperature. A solution of triethanolamine (0.88 g) in tetrahydrofuran (5 mL) was added dropwise to the reaction mixture. After being stirred under reflux for 5 hrs, water was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium-pressure silica gel column chromatography (eluent: ethyl acetate/ethanol=15/1) to afford the title compound (1.13 g).

Provenance & Evidence