Реакция #8227

Уравнение реакции

methanol

boron tribromide

methyl 4-({(5-ethoxy-5-oxopentyl)[2-(5-fluoro-2-methoxy-phenyl)ethyl]amino}methyl)benzoate

→

Methyl 4-({(5-methoxy-5-oxopentyl)[2-(5-fluoro-2-hydroxyphenyl)-ethyl]amino}methyl)benzoate

Растворители

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   Температураthe reaction mixture is heated
2. 2
   Температураat reflux overnight
3. 3
   ТемператураThe mixture is cooled
4. 4
   Другоеthe solvents are evaporated under reduced pressure
5. 5
   Промывкаwashed with sodium carbonate
6. 6
   Экстракцияthe aqueous phase is extracted three times with ethyl acetate
7. 7
   Промывкаthe combined organic phases are washed with saturated sodium chloride solution
8. 8
   Сушкаdried over magnesium sulphate
9. 9
   Фильтрацияfiltered
10. 10
    Концентрированиеconcentrated
11. 11
    ДругоеThe residue is chromatographed over silica gel (cyclohexane:ethyl acetate (5:1) to ethyl acetate: methanol (9:1))

Методика

2.6 g (5.84 mmol) of methyl 4-({(5-ethoxy-5-oxopentyl)[2-(5-fluoro-2-methoxy-phenyl)ethyl]amino}methyl)benzoate are dissolved in 50 ml of dichloromethane, the mixture is cooled to 0° C., and 19.3 ml (19.3 mmol) of a 1N solution of boron tribromide in dichloromethane are added dropwise. The solution is stirred at 0° C. for one hour. 50 ml of methanol are slowly added dropwise at 0° C., and the reaction mixture is heated at reflux overnight. The mixture is cooled and the solvents are evaporated under reduced pressure. The residue is taken up in ethyl acetate and washed with sodium carbonate, the aqueous phase is extracted three times with ethyl acetate and the combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulphate, filtered and concentrated. The residue is chromatographed over silica gel (cyclohexane:ethyl acetate (5:1) to ethyl acetate: methanol (9:1)).

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