Nitroxyl → HCID 565757, compound

Participants

Reaction Conditions

Reaction Steps

Into a solution of 2.85 g (35 mmol) of cyclohexene in 20 mL of tetrahydrofuran at ambient temperature under nitrogen is added dropwise 12.5 mL (12.5 mmol) of a 1M tetrahydrofuran solution of borane. During addition, reaction temperature is kept under 35° C. Reaction mixture, after addition, is then heated to 40° C. for 2 hours. After cooled to ambient temperature, the reaction is added dropwise into a suspension of 2.15 g (12.5 mmol) of 4-hydroxy-2,2,6,6-tetramethyl-piperidine-1-oxyl, 1.50 g (37.5 mmol) of sodium hydroxide and 3.17 g (18.8 mmol) of silver nitrate in 40 mL of water at ambient temperature under nitrogen. Thin layer chromatography detects no more starting nitroxyl after 2 hours. Reaction mixture is extracted with 2×10 mL of ethyl acetate and dried over sodium sulfate. Filtration removes inorganic and filtrate is concentrated to an off-white oil. Purification of product by dry-column flash chromatography (20:80/ ethyl acetate:heptane eluent) gives 3.14 g of a white crystalline solid in 98.7% yield: 1H NMR (CDCL3)(300.08 MHz)δ 1.15 (s, CH3, 6 H), 1.20 (s, CH3 ,6H), 1.22, 1.46 (m, CH2, 4H), 1.76, 1.81 (m, CH2, 10H)3.60 (m, CH, 1H),3.90 (m, CH, 1H); MS [M+1]256.

Provenance & Evidence