Tosylmethyl isocyanide → HCID 66887446, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-(dimethylamino)-4-(3-methoxyphenyl)cyclohexanone (2.47 g, 10 mmol) and tosylmethyl isocyanide (2.54 g, 13 mmol) in anhydrous 1,2-dimethoxyethane (40 ml) and anhydrous ethanol (2 ml) was cooled to −30° C. A solution of potassium tert-butylate (2.70 g, 24 mmol) in anhydrous tetrahydrofuran (20 ml) was then added dropwise such that the internal temperature did not rise above 5° C. The mixture was stirred at 0° C. for 1 h, at room temperature for 24 h and then under reflux for 5 h. The reaction mixture was cooled to room temperature and filtered. The residue on the filter was washed with 1,2-dimethoxyethane. The filtrate was concentrated i. vac., the residue was taken up in diethyl ether and the solution was washed with water (3×20 ml) and saturated sodium chloride solution (20 ml). The organic phase was dried with sodium sulfate and concentrated i. vac. The crude product (1.76 g) was purified by flash chromatography with ethyl acetate and then ethyl acetate/methanol (9:1→8:2).

Provenance & Evidence