Hydroxylamine → 1,1-Dimethylethyl 4-[4-(4,5-dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl)-1-piperidinecarboxylate

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1,1-dimethylethyl 4-(4-formyl-2-thiazolyl)-1-piperidinecarboxylate (1.0 g, 3.4 mmol) in ethanol (5 mL) was added an aqueous solution of hydroxylamine (50 wt. %, 0.25 mL, 4.0 mmol). The reaction mixture was heated at 60° C. for 1 h, during which time the reaction mixture became homogeneous. The resulting reaction solution was cooled to room temperature and diluted with tetrahydrofuran (10 mL). Styrene (0.57 mL, 5 mmol) was added to the reaction mixture, followed by a portionwise addition of Clorox® (aqueous sodium hypochlorite solution) (10.5 mL) over 3 h. The reaction mixture was stirred overnight at room temperature, and then filtered. The solid collected by filtration was washed with water, diethyl ether and air dried to give the title compound as a white powder (610 mg). The filtrate was diluted with saturated aqueous sodium bicarbonate solution and extracted with diethyl ether. The extract was dried (MgSO4) and concentrated under reduced pressure to give more of the title compound as a yellow oil (850 mg). The oil was diluted with diethyl ether (4 mL) and upon standing provided the title compound as a white solid (233 mg).

Provenance & Evidence