Phosphorus oxychloride → HCID 19043054, compound

Participants

Reaction Steps

N-Formyl-N-(benzocycloheptan-1-yl)ethylamine (0.39 g, 1.81 mmol) was treated with phosphorus oxychloride (0.17 ml, 1.81 mmol) at room temperature under argon. After 30 minutes, 1,2-dichloroethane (1.2 ml) was added at 0° C. followed by a solution of 2-(2-methoxy-5-ethylsulfonylphenyl)-1H-pyrrole (0.4 g, 1.51 mmol) in 1,2-dichloroethane (4 ml). The mixture was allowed to warm to room temperature and stirred for 16 h at 25° C. and then for 6 h at 40° C. Sodium borohydride (0.55 g, 14.5 mmol) was then added at 0° C., and the reaction mixture was warmed to room temperature and stirred for 3 h. Water (2.4 ml) and then methanol (2.4 ml) were added dropwise. More water (30 ml) was added and the borane complex was extracted with dichloromethane (3×30 ml). The combined organics were dried (Na2SO4) and evaporated to an oil which was then treated with methanol (4.8 ml) and conc. HCl (2.4 ml) at room temperature for 16 h. The mixture was diluted with water (25 ml) and basified with 40% aqueous NaOH. Extraction into dichloromethane (3×30 ml), followed by drying (Na2SO4) and evaporation of the organic extracts gave an orange oil (0.73 g). The crude material was purified by chromatography on silica eluting with ethyl acetate (20-50%)--hexane, to give the title compound as an orange oil (0.31 g, 44%)

Provenance & Evidence