HCID 70819237, compound → HCID 86680967, compound

Participants

Reaction Steps

Di tert-butyl 2-[4-(hydroxymethyl)phenyl]piperazine-1,4-dicarboxylate (750 mg, 1.911 mmol) was dissolved in dichloromethane (12.00 mL) and dioxomanganese (1.993 g, 396.5 μL, 22.93 mmol) was added. The reaction was stirred at ambient temperature for 22 hours. Reaction followed by TLC. Reaction mixture was filtered through a pad of celite and washed with dichloromethane. Purified by column chromatography (ISCO Companion, 40 g column) dry loaded and eluted with 5 to 50% ethyl acetate/petroleum ether. Product fractions were combined and concentrated in vacuo to give the sub-title product. (699 mg, 94% yield). 1H NMR (400.0 MHz, CDCl3) δ 1.43-1.47 (m, 18H), 3.01 (br s, 2H), 3.43-3.44 (m, 1H), 3.98-4.01 (m, 2H), 4.44 (br s, 1H), 5.32 (br s, 1H), 7.49-7.51 (m, 2H), 7.87 (d, 2H) and 10.03 (s, 1H) ppm; TLC (petroleum ether: ethyl acetate, 1:1 v/v) Rf=0.61

Provenance & Evidence