Реакция #424786

Уравнение реакции

Methyl 3-[2-(acetylamino)ethyl]-naphthalenecarboxylate

lithium borohydride

→

title compound

N-{2-[4-(Hydroxymethyl)-2-naphthalenyl]ethyl}acetamide

Растворители

ether

THF

Условия реакции

Обработка

1. 1
   ДругоеThe reaction mixture thus obtained
2. 2
   Другоеcarefully quenched with 1 N aq. HCl
3. 3
   ДругоеThe aqueous layer was separated
4. 4
   Экстракцияback-extracted with EtOAc
5. 5
   ПромывкаThe combined organic extracts were washed further with 1 N aq. NaOH, water and brine
6. 6
   Сушкаdried over Na2SO4
7. 7
   Фильтрацияfiltered

Методика

Methyl 3-[2-(acetylamino)ethyl]-naphthalenecarboxylate (1 eq.) from the previous step was taken up in THF (0.18 M). To this solution was then added lithium borohydride (12 eq.) and the resulting solution was vigorously stirred at 50° C. for 5 h. The reaction mixture thus obtained was diluted further with ether and carefully quenched with 1 N aq. HCl. The aqueous layer was separated and back-extracted with EtOAc. The combined organic extracts were washed further with 1 N aq. NaOH, water and brine, dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound as a white solid.

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