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

Temperature

90 °C

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).

1. extractionextracted with ethyl acetate (2×400 ml)
2. washwashed successively with water (2×100 ml) and brine (1×100 ml)
3. dry with materialdried over magnesium sulfate
4. concentrationconcentrated in vacuo
5. customto furnish an oil

ORD record

ord-f7da4e9d0ce94930a8ea36ac1bf39293

Source dataset

uspto-grants-2005_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06919460B2