Реакция #49303

Уравнение реакции

4-chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

hydrochloric acid

4-piperidineethanol

acetic acid

sodium triacetoxyborohydride

→

4-chloro-7-{1-(tert-butoxycarbonyl)-5-[4-(2-hydroxyethyl)piperidinomethyl]indol-2-yl}isoindolinone

Выход 110.3%

Растворители

acetonitrile

ethyl acetate

Условия реакции

Обработка

1. 1
   Экстракцияby extracting with 1 mol/L hydrochloric acid
2. 2
   workup.ADDITIONThe aqueous layer was added with sodium carbonate
3. 3
   ЭкстракцияThe mixture was extracted with ethyl acetate
4. 4
   ПромывкаThe organic layer was washed with saturated brine
5. 5
   Сушкаdried over anhydrous sodium sulfate
6. 6
   ДругоеThe solvent was evaporated under reduced pressure

Методика

In a similar manner to Step 2 of Example 6, 4-chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (30.0 mg, 0.0730 mmol) was dissolved in acetonitrile (2 mL), and the solution was treated with 4-piperidineethanol (94 mg, 0.73 mmol), acetic acid (0.168 mL, 2.93 mmol) and sodium triacetoxyborohydride (54 mg, 0.26 mmol). The reaction mixture was added with 1 mol/L hydrochloric acid and ethyl acetate, followed by extracting with 1 mol/L hydrochloric acid. The aqueous layer was added with sodium carbonate to adjust the pH to 9. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain 4-chloro-7-{1-(tert-butoxycarbonyl)-5-[4-(2-hydroxyethyl)piperidinomethyl]indol-2-yl}isoindolinone (42.2 mg).

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