Methane → HCID 86652735, compound

Participants

Reaction Steps

A solution of tert-butyl 4-(aminooxy)piperidine-1-carboxylate (2.0 g, 9.2 mmol) in tetrahydrofuran (10 ml) was added over 30 minutes to a suspension of trichloromethyl chloroformate (2.74 g, 13.8 mmol) and activated charcoal (20 mg) in tetrahydrofuran (35 ml) at 0° C. over 30 minutes. After stirring at room temperature for 17 hours, the reaction mixture was filtered over silicagel and the filtrate was concentrated in vacuo. The residue was dissolved in tetrahydrofuran (15 ml), 4-fluoroaniline (2.0 g, 18.4 mmol) and N,N-diisopropylethylamine (3.58 g, 27.6 mmol) were added and the whole was stirred at room temperature for 17 hours. The reaction mixture was concentrated in vacuo and the residue was diluted with ethyl acetate (50 ml), washed with H2O (20 ml×2), brine (20 ml×2), dried over Na2SO4 and concentrated in vacuo. The residual solid was recrystallized from diethyl ether to give tert-butyl 4-(3-(4-fluorophenyl)ureidooxy)piperidine-1-carboxylate (2.19 g, 67%) as a white solid: LCMS: 354 [M+1]+.

Provenance & Evidence