Реакция #76091

Уравнение реакции

3-[4-(2-heptylamino-ethyl)-phenyl]-2,2-dimethyl-propionic acid ethyl ester

boron tribromide

H2O

boron tribromide

→

3-[4-(2-heptylamino-ethyl)-phenyl]-2,2-dimethyl-propionic acid

Растворители

methylene chloride

dichloromethane

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was warmed to room temperature
2. 2
   ТемператураThe mixture was cooled to −78° C.
3. 3
   ТемператураThe mixture was warmed to room temperature
4. 4
   workup.STIRRINGstirred for 20 minutes
5. 5
   Экстракцияextracted with dichloromethane (3×)
6. 6
   Сушкаdried over anhydrous sodium sulfate
7. 7
   Концентрированиеconcentrated to a clear film
8. 8
   workup.DISSOLUTIONThis was dissolved in dioxane/2M HCl (10 mL/10 mL)
9. 9
   Температураwas refluxed for 20 minutes
10. 10
    ТемператураThe mixture was cooled
11. 11
    ПромывкаThe basic solution was washed with diethyl ether (3×)
12. 12
    ЭкстракцияThe acidic solution was extracted with diethyl ether (3×)
13. 13
    Промывкаwashed with brine (2×)
14. 14
    Сушкаdried over anhydrous sodium sulfate
15. 15
    Концентрированиеconcentrated

Методика

To a solution of the impure 3-[4-(2-heptylamino-ethyl)-phenyl]-2,2-dimethyl-propionic acid ethyl ester (100 mg of the mixture) dissolved in methylene chloride (5 mL) cooled to −78° C. under a nitrogen atmosphere was added boron tribromide (1M in dichloromethane, 0.432 mL). The mixture was warmed to room temperature and stirred for 3 h. The mixture was cooled to −78° C. and an additional 0.432 mL of the 1M boron tribromide in dichloromethane was added. The mixture was warmed to room temperature and stirred for 20 minutes. The mixture was poured over H2O (10 mL) and extracted with dichloromethane (3×). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated to a clear film. This was dissolved in dioxane/2M HCl (10 mL/10 mL) and was refluxed for 20 minutes. The mixture was cooled and brought to pH 10 with 2 N NaOH. The basic solution was washed with diethyl ether (3×) and brought to pH 4 with 2N HCL. The acidic solution was extracted with diethyl ether (3×), washed with brine (2×), dried over anhydrous sodium sulfate and concentrated to give 3-[4-(2-heptylamino-ethyl)-phenyl]-2,2-dimethyl-propionic acid as a clear film (23 mg, 46%).

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