Hydrogen Peroxide → HCID 118173835, compound

Participants

Reaction Steps

To a solution of tert-butyl 6-oxo-7-azaspiro[4.5]dec-2-ene-7-carboxylate (0.61 g, 2.44 mmol) in anhydrous THF (5 mL) was added borane-methyl sulfide complex (10.0 M, 2.45 mL, 24.5 mmol) at 0° C. After stirring for 10 min, the reaction mixture was warmed to rt and stirred overnight, then cooled down to 0° C. and a mixture of NaOH aqueous solution (3 M, 3 mL, 9 mmol) and H2O2 (30% in water, 3 mL) was added. After stirring for 5 min, the reaction mixture was heated to reflux for 5 h, then cooled down to rt and concentrated in vacuo. The residue was dissolved in water (10 mL), and extracted with EtOAc (15 mL×3). The combined organic phases were washed with brine (50 mL), and dried over anhydrous Na2SO4, then concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/5) to give the title compound as colorless oil (252 mg, 41%).

Provenance & Evidence