Tert-Butyl nitrite → HCID 21201855, compound

Participants

Reaction Steps

Potassium tert-butoxide (57.8 g) was added to 1-methoxymethyl-2-oxo-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (29.1 g) in absolute toluene (1 litter) at 0° C. The resultant mixture was stirred for 30 minutes at 0° C., and tert-butyl nitrite (31.9 g) was added thereto, followed by stirring for 18 hours at room temperature. Ice-water was added to the reaction mixture for separation of layers, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform:methanol=25:1), to thereby obtain 22.8 g of the title compound as a light brown oily substance (yield: 71.1%).

Provenance & Evidence