Reacción #5458

Ecuación de reacción

lithium aluminum hydride tetrahydrofuran

water

sodium hydroxide

water

1-azabicyclo[3.2.1]octane-5-carboxylic acid ethyl ester

→

1-Azabicyclo[3.2.1]octane-5-methanol

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturarefluxed for one hour
2. 2
   Temperaturacooled (0° C.)
3. 3
   Filtraciónthe mixture was filtered through Celite (the solid
4. 4
   Lavadowas washed with tetrahydrofuran) and
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   Otroto afford 6.50 g (92%) of viscous, colorless oil, which
7. 7
   Temperaturaon cooling

Procedimiento

A cooled (0° C.) solution of 1.0N lithium aluminum hydride/tetrahydrofuran (55 mL, 55 mmol) under nitrogen was treated dropwise with a solution of 1-azabicyclo[3.2.1]octane-5-carboxylic acid ethyl ester (9.17 g, 50 mmol) in anhydrous tetrahydrofuran (20 mL), stirred for 30 minutes at room temperature, refluxed for one hour, and cooled (0° C.). In sequence, water (2.1 mL), 15% sodium hydroxide solution (2.1 mL) and water (6.3 mL) were carefully added dropwise, and the mixture was filtered through Celite (the solid was washed with tetrahydrofuran) and concentrated in vacuo to afford 6.50 g (92%) of viscous, colorless oil, which can be used as is or can be solidified on cooling; mp 44°-47° C.

Fuente