反应详情

温度

-30 °C

A solution of methyl 4-[(2-{(5R)-2-oxo-5-[(1E)-3-oxooct-1-enyl]pyrrolidin-1-yl}ethyl)thio]-butanoate (0.039 g, 0.1 mmol) in 2 mL of anhydrous toluene was added dropwise to a −30° C. solution of (R)-2-methyl-CBS-oxazaborolidine (1 M in toluene, 0.05 mL, 0.05 mmol) and borane-methyl sulfide complex (10 M, 0.01 mL, 0.1 mmol). The reaction was stirred for 7 hours at −30° C. and then a solution of hydrochloric acid in methanol (2 M, 1-2 mL) was added. The solution was warmed to room temperature and the solvents were removed via reduced pressure. The crude residue was purified via chromatography yielding 11 mg of 4-[(2-{(2R)-2-[(1E,3S)-3-hydroxyoct-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)thio]butanoic acid methyl ester as an oil. This was taken directly on to the next step.

1. temperatureThe solution was warmed to room temperature
2. customthe solvents were removed via reduced pressure
3. customThe crude residue was purified via chromatography