Reacción #11530

Ecuación de reacción

lithium aluminum hydride

1-adamantaneacetic acid N-methylamide

lithium aluminum hydride

Ethyl acetate

→

titled compound

Rendimiento 66.0%

2-(1-Adamantyl)-N-methylethylamine

Rendimiento 66.0%

Disolventes

tetrahydrofuran

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling over five minutes
2. 2
   TemperaturaThe mixture was refluxed for six hours
3. 3
   Temperaturacooling again
4. 4
   Extracciónthe whole was extracted with 1 N hydrochloric acid (50 ml) twice
5. 5
   workup.ADDITIONA 4 N aqueous sodium hydroxide solution was added to the
6. 6
   Extracciónextract
7. 7
   Extracciónthe whole was extracted with diethyl ether (80 ml)
8. 8
   LavadoThe organic layer was washed with a saturated aqueous sodium chloride solution (60 ml)
9. 9
   Secadodried over magnesium sulfate
10. 10
    OtroThe solvent was evaporated under reduced pressure

Procedimiento

A solution of 1-adamantaneacetic acid N-methylamide (1.54 g, 7.45 mmol) in tetrahydrofuran (15.0 ml) was added dropwise to a solution of lithium aluminum hydride (569 mg, 15.0 mmol) in diethyl ether (34.0 ml) under ice-cooling over five minutes. The mixture was refluxed for six hours and then stirred under ice-cooling again. Ethyl acetate was added to the reaction mixture to treat excess lithium aluminum hydride, and then the whole was extracted with 1 N hydrochloric acid (50 ml) twice. A 4 N aqueous sodium hydroxide solution was added to the extract to basify it, and the whole was extracted with diethyl ether (80 ml). The organic layer was washed with a saturated aqueous sodium chloride solution (60 ml) and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give 890 mg (66%) of the titled compound.

Fuente