Hydrogen Peroxide → HCID 57485794, compound

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%).

1. temperaturecooled in ice bath
2. stirringthe mixture stirred overnight at ambient temperature
3. extractionThe mixture was extracted with ether (2×50 mL)
4. washthe combined extracts were washed with water and brine (25 mL each)
5. dry with materialDrying over anhydrous magnesium sulfate
6. filtrationfollowed by filtration and concentration under reduced pressure

ORD record

ord-7e216adeb0a4473fbd75fced32a213e2

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07402592B2