Reacción #1256753

Ecuación de reacción

trifluoroacetic acid

BF3.Et2O

methanesulfonic acid

triethylsilane

Compound 29

4-(3-Ethoxycarbonyl-propyl)-5-oxo-1-(4-methylphenylsulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-4-carboxylic acid ethyl ester

→

compound 30

Rendimiento 53.0%

4-(3-Ethoxycarbonyl-propyl)-1-(4-methylphenylsulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-4-carboxylic acid ethyl ester

Rendimiento 53.0%

Disolventes

1,2-dichloroethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato slowly warm to room temperature over 18 hours
2. 2
   TemperaturaThe reaction was cooled to 5° C.
3. 3
   Otrocautiously quenched with saturated aqueous NaHCO3 (100 mL)
4. 4
   ExtracciónThe reaction mixture was extracted with ethyl acetate (100 mL)
5. 5
   Extracciónthe ethyl acetate extract
6. 6
   Extracciónwas extracted with saturated aqueous NaHCO3, water, brine (2×)
7. 7
   Secadodried over Na2SO4
8. 8
   Concentraciónconcentrated in vacuo
9. 9
   Otroto give an oil
10. 10
    OtroThis oil was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (17:3)

Procedimiento

Compound 29 (4.76 g, 9.48 mmol) was dissolved in 45 mL of dry 1,2-dichloroethane, cooled to 5° C., and treated with trifluoroacetic acid (1.3 mL), BF3.Et2O (1.4 mL), anhydrous methanesulfonic acid (3.2 mL) and triethylsilane (5.7 mL). The reaction was allowed to slowly warm to room temperature over 18 hours. The reaction was cooled to 5° C. and cautiously quenched with saturated aqueous NaHCO3 (100 mL). The reaction mixture was extracted with ethyl acetate (100 mL) and the ethyl acetate extract was extracted with saturated aqueous NaHCO3, water, brine (2×), dried over Na2SO4, and concentrated in vacuo to give an oil. This oil was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (17:3) to give 2.43 g (53%) of compound 30 as a colorless oil.

Fuente