Hydrogen Peroxide → HCID 57485794, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 3-azabicyclo[3.3.1]non-6-ene-3-carboxylate (2.50 g, 12.8 mmol) in 75 mL of THF was cooled in an ice bath and borane-THF (1M in THF, 19 mL, 19 mmol) was added drop-wise. The reaction was stirred at about 10° C. for 3.5 h, then cooled in ice bath. A solution of sodium hydroxide (2.4 g, 60 mmol) in 10 mL water was added drop-wise, followed immediately by an additional 50 mL of THF and 10 mL of water. Hydrogen peroxide (30% aqueous, 8.5 g, 75 mmol) was then added, and the mixture stirred overnight at ambient temperature. The mixture was extracted with ether (2×50 mL), and the combined extracts were washed with water and brine (25 mL each). Drying over anhydrous magnesium sulfate, followed by filtration and concentration under reduced pressure, gave the product as a colorless, viscous oil (2.2 g, 80%).

Provenance & Evidence