Reacción #7517

Ecuación de reacción

lithium aluminum hydride

(RS)-indoline-2-carboxylic acid

ethanol

hydrochloric acid

→

title compound

Rendimiento 64.3%

(RS)-2-hydroxymethylindoline

Rendimiento 64.3%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe reaction mixture was stirred under ice-
2. 2
   Temperaturacooling
3. 3
   FiltraciónThe precipitate was filtered off
4. 4
   Lavadothe mother liquor was washed with saturated brine
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   OtroThe solvent was evaporated under reduced pressure
7. 7
   Lavadoeluted with ethyl acetate-hexane (1:4-1:1)

Procedimiento

To a solution of (RS)-indoline-2-carboxylic acid (8.16 g, 50 mmol) in tetrahydrofuran (50 ml) was added under ice-cooling lithium aluminum hydride (5.7 g, 150 mmol) and the mixture was stirred at 60° C. for 18 h. The reaction mixture was stirred under ice-cooling and ethanol and 1N hydrochloric acid were added. The precipitate was filtered off and the mother liquor was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was applied to silica gel column chromatography and eluted with ethyl acetate-hexane (1:4-1:1) to give the title compound (4.8 g, 64%).

Fuente