Water → (R)-2-bromo-1-pyridin-3-yl-ethanol

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 1.24 g (3.91 mmol) of (R)-3-(2-bromo-1-(tert-butyl-dimethyl-silanyl)-ethyl)-pyridine, 1.6 g (7.83 mmol) of 2-(4-oxazol-4-yl-phenoxy)-ethylamine, and 1.4 ml (7.83 mmol) of diisopropylethylamine in 20 ml of dry dimethylsulfoxide was heated at about 90° C. for about 18 hours. The mixture was poured into 400 ml of water and extracted with ethyl acetate (2×400 ml). The organic extracts were combined, washed successively with water (2×100 ml) and brine (1×100 ml), dried over magnesium sulfate, and concentrated in vacuo to furnish an oil. Chromatography on silica gel eluting with methanol:dichloromethane (1:19, v/v) yielded 963 mg (56% yield) of the title compound as an amber-colored oil, αD=−45.7° (c=0.49, chloroform).

Provenance & Evidence