Ammonium nitrate → HCID 70664206, compound

Participants

Reaction Steps

To a solution of benzyl 7-azabicyclo[4.1.0]heptane-7-carboxylate (see Example 13, 0.273 g, 1.18 mmol) in 3 mL of THF was added eerie ammonium nitrate (0.065 g, 0.12 mmol) and sodium thiomethoxide (0.165 g, 2.36 mmol). After 30 min, 15-crown-5 (0.520 g, 2.36 mmol) was added. After 110 h, the reaction was concentrated in vacuo, diluted with water, and extracted 3× with diethyl ether. The combined organic fractions were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-15% ethyl acetate in hexanes to provide benzyl rac-[(1R,2R)-2-(methylthio)cyclohexyl]carbamate that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 280.1 for [M+H]+.

Provenance & Evidence