Hydrogen Peroxide → HCID 18009116, compound

Participants

Reaction Steps

To a solution of the olefin from Step J (1.303 g, 5.11 mmol) in 10 mL of THF at 0° C. was added a solution of 9-borabicyclo[3.3.1]nonane in THF (50 mL, 25.5 mmol, 0.5 M). After one hour, the reaction was warmed to room temperature for 3 hours, then recooled to 0° C. A solution (20 mL) of sat. aq. NaHCO3 and 30% aq. H2O2 (2:1) was added, and the reaction was warmed to room temperature. After 30 minutes, the mixture was partitioned between CHCl3 and aq. NaHCO3 solution, and the aqueous phase was extracted with CHCl3. The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. Purification by silica gel chromatography (5-8% MeOH/CH2Cl2, then rechromatographed using 50-100% acetone/CH2Cl2) provided the titled compound as a pale yellow oil.

Provenance & Evidence