Реакция #1256753

Уравнение реакции

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

Выход 53.0%

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

Выход 53.0%

Растворители

1,2-dichloroethane

Условия реакции

Обработка

1. 1
   Температураto slowly warm to room temperature over 18 hours
2. 2
   ТемператураThe reaction was cooled to 5° C.
3. 3
   Другоеcautiously quenched with saturated aqueous NaHCO3 (100 mL)
4. 4
   ЭкстракцияThe reaction mixture was extracted with ethyl acetate (100 mL)
5. 5
   Экстракцияthe ethyl acetate extract
6. 6
   Экстракцияwas extracted with saturated aqueous NaHCO3, water, brine (2×)
7. 7
   Сушкаdried over Na2SO4
8. 8
   Концентрированиеconcentrated in vacuo
9. 9
   Другоеto give an oil
10. 10
    ДругоеThis oil was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (17:3)

Методика

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.

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