Hydrogen Peroxide → HCID 44194661, compound

Participants

Reaction Steps

To a solution of 3-((S)-1-((S)-1-(4-bromophenyl)ethyl)-2-oxo-4-phenylpiperidin-4-yl)-2,2-dimethylpropanenitrile (11 mg, 0.025 mmol) in DMSO (3 mL) were added K2CO3 (6.9 mg 0.05 mmol) and 30% H2O2 (5.7 mg 0.05 mmol). The mixture was stirred at rt overnight. After being diluted with water (2 mL), the mixture was washed with EtOAc (3×2 mL). The aqueous layer was acidified to pH=3-4, and extracted with EtOAc (3×2 mL). The combined organic layers were washed with brine (3×2 mL), dried over anhydrous Na2SO4, filtered, and concentrated under vacuum. The crude product was dried under vacuum and purified by TLC and preparative HPLC to give 3-((S)-1-((S)-1-(4-bromophenyl)ethyl)-2-oxo-4-phenylpiperidin-4-yl)-2,2-dimethylpropanamide (8 mg, 70%). LC-MS Method 2 tR=1.36 min, m/z=481, 479, 459, 457; 1H NMR (CDCl3): δ 0.78 (s, 3H), 1.08 (s, 3H), 1.40 (d, 3H), 2.0 (m, 4H), 2.18 (m, 1H), 2.66 (m, 1H), 2.81 (m, 1H), 3.32 (m, 1H), 5.58 (m, 1H), 5.84 (m, 1H), 6.18 (m, 1H), 6.68 (m, 2H), 7.16 (m, 2H), 7.20 (m, 5H).

Provenance & Evidence