Реакция #2004592

Уравнение реакции

sodium bis(2-methoxyethoxy)aluminum hydride

(1S,5S)-1-amino-7-methylene-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octane

sodium hydroxide

→

title compound

Выход 97.4%

(1S,5R)-1-Amino-7-methylene-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octane

Выход 97.4%

Растворители

toluene

toluene

Условия реакции

Обработка

1. 1
   workup.STIRRINGwith stirring under ice-
2. 2
   Температураcooling
3. 3
   Экстракцияfollowed by extraction with toluene (30 ml×1, 20 ml×1)
4. 4
   ПромывкаThe organic layer was washed with brine
5. 5
   Сушкаdried over anhydrous sodium sulfate
6. 6
   ФильтрацияAfter filtration
7. 7
   Концентрированиеthe filtrate was concentrated under reduced pressure

Методика

A 65% solution of sodium bis(2-methoxyethoxy)aluminum hydride in toluene (0.539 ml, 1.79 mmol) was added to a solution of (1S,5S)-1-amino-7-methylene-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octane (115 mg, 0.449 mmol) in toluene (2.24 ml), and the mixture was stirred at room temperature for 30 minutes and at 80° C. for 30 minutes. A 5 mol/l sodium hydroxide solution (15.0 ml) was added to the reaction solution with stirring under ice-cooling, followed by extraction with toluene (30 ml×1, 20 ml×1). The organic layer was washed with brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to give 106 mg of the title compound.

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