Hydroxyamine hydrochloride → 3-[tert-butyl(diphenyl)silyl]oxy-N'-hydroxypropanimidamide

Participants

Reaction Steps

To a solution of 3-{[tert-butyl(diphenyl)silyl]oxy}propanenitrile (4.4 g, 14.2 mmol) in methanol (40 ml) was added hydroxylamine hydrochloride (8.9 g, 128 mmol) and sodium bicarbonate (11.9 g, 142 mmol). The mixture was heated at reflux for 48 hours. The mixture was then cooled to room temperature, the solvent was evaporated, ice water was added, and the resulting solution was extracted with ethyl acetate (2×). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting residue was purified via silica gel chromatography (50-100% ethyl acetate in hexanes) to afford the title compound.

Provenance & Evidence