Trifluoroacetic acid → HCID 10198334, compound

Temperature

2.5 °C

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.

1. concentrationThe solution was then concentrated by rotary evaporation
2. customby further drying under high vacuum
3. temperatureThe resulting red oil was cooled (0-5° C.)
4. additiontreated with saturated NaCI solution (10 mL)
5. extractionextracted with CHCl3 (6×20 mL)
6. washThe combined CHCl3 extracts were washed with saturated NaCl solution (25 mL)
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated by rotary evaporation
10. customby further drying under high vacuum

ORD record

ord-d7187324986b4c159dae4a6a4f88c360

Source dataset

uspto-grants-2002_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06337351B1