Hydrogen Peroxide → HCID 86619146, compound

Participants

Reaction Steps

24.2 mg of the t-butyl[(1S)-1-(4-vinylphenyl)ethyl]carbamate [152-1] was dissolved in 1 mL of tetrahydrofuran, then 783 μL of 9-borabicyclo[3.3.1]nonane (9-BBN, 0.5M tetrahydrofuran solution) was added dropwise over 2 minutes under an ice-cold condition, and stirred overnight at room temperature. Thereto, 0.2 mL of a 3N aqueous solution of sodium hydroxide and 0.2 mL of hydrogen peroxide solution (35%) were added, and stirred at room temperature for 10 hours. The reaction mixture was added with water and extracted with chloroform, and the organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by preparative thin-layer chromatography. The obtained compound was dissolved in 1.5 mL of N,N-dimethylformamide, then 14.2 mg of benzoic acid and 21.3 mg of 4-dimethylaminopyridine were added and stirred to homogenize the solution, and 22.3 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added and stirred overnight at room temperature. Thereto, water was added, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the thus obtained residue was purified by preparative thin-layer chromatography, to obtain 15.2 mg of 2-(4-{(1S)-1-[(t-butoxycarbonyl)amino]ethyl}phenyl)ethylbenzoate [152-2] as a white solid.

Provenance & Evidence