Réaction #1256753

Équation de réaction

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

Rendement 53.0%

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

Rendement 53.0%

Solvants

1,2-dichloroethane

Conditions de réaction

Traitement

1. 1
   Températureto slowly warm to room temperature over 18 hours
2. 2
   TempératureThe reaction was cooled to 5° C.
3. 3
   Autrecautiously quenched with saturated aqueous NaHCO3 (100 mL)
4. 4
   ExtractionThe reaction mixture was extracted with ethyl acetate (100 mL)
5. 5
   Extractionthe ethyl acetate extract
6. 6
   Extractionwas extracted with saturated aqueous NaHCO3, water, brine (2×)
7. 7
   Séchagedried over Na2SO4
8. 8
   Concentrationconcentrated in vacuo
9. 9
   Autreto give an oil
10. 10
    AutreThis oil was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (17:3)

Mode opératoire

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.

Source