Reacción #410400

Ecuación de reacción

1-(3,4,5-trimethoxybenzoyl)-3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)pyrrolidine

dichloromethane pyridine

acetic anhydride

→

1-(3,4,5-trimethoxybenzoyl)-3-(3,4-dichlorophenyl)-3-(2-acetoxyethyl)pyrrolidine

Disolventes

ethyl acetate

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónconcentrate the reaction mixture in vacuo
2. 2
   Otroto obtain a residue
3. 3
   Extracciónextract with 1M hydrochloric acid solution (2×200 mL), saturated sodium bicarbonate solution, and saturated sodium chloride solution
4. 4
   SecadoDry the organic layer over MgSO4
5. 5
   Filtraciónfilter
6. 6
   Concentraciónconcentrate in vacuo
7. 7
   Otroto obtain a residue

Procedimiento

Combine 1-(3,4,5-trimethoxybenzoyl)-3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)pyrrolidine (4.5 g, 9.9 mmol) and dichloromethane/pyridine (70 mL, 6/1). Add acetic anhydride (1.04 mL, 11.0 mmol) and 4-dimethylaminopyridine (50 mg, 0.41 mmol). After 2 hours, concentrate the reaction mixture in vacuo to obtain a residue. Dissolve the residue in ethyl acetate and extract with 1M hydrochloric acid solution (2×200 mL), saturated sodium bicarbonate solution, and saturated sodium chloride solution. Dry the organic layer over MgSO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with ethyl acetate to give 1-(3,4,5-trimethoxybenzoyl)-3-(3,4-dichlorophenyl)-3-(2-acetoxyethyl)pyrrolidine: Rf=0.38 (silica gel, ethyl acetate). Elemental Analysis calculated for C24H27Cl2NO6: C 58.07; H 5.48; N 2.82; Found: C 57.67; H 5.46; N 2.84.

Fuente