Trifluoroacetic acid → HCID 10198334, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, a cold (0-5° C.), stirring solution of (4E)-N-methyl-N-(tert-butoxycarbonyl)-5-(3,4-methylenedioxyphenyl)-4-penten-2-amine (1.08 g, 3.38 mmol) in anisole (11 mL) was treated drop-wise over 45 min with trifluoroacetic acid (16.28 g, 142.8 mmol). The resulting solution was stirred for 1.5 h at 0-5° C. The solution was then concentrated by rotary evaporation followed by further drying under high vacuum. The resulting red oil was cooled (0-5° C.), basified with 10% NaOH solution (15 mL), treated with saturated NaCI solution (10 mL) and extracted with CHCl3 (6×20 mL). The combined CHCl3 extracts were washed with saturated NaCl solution (25 mL), dried (Na2SO4), filtered, concentrated by rotary evaporation, followed by further drying under high vacuum to produce a brown oil (0.87 g). The crude product was purified by column chromatography on silica gel (50 g), eluting with CH3OH—Et3N (98:2, v/v). Selected fractions containing the product (Rf 0.37) were combined and concentrated on a rotary evaporator. The residue was dissolved in CHCl3. The CHCl3 solution was dried (Na2SO4), filtered, concentrated by rotary evaporation and dried under high vacuum to give 380.3 mg (51.3%) of a light-yellow oil.

Provenance & Evidence