Reacción #74269

Ecuación de reacción

(S)-indoline-2-carboxylic acid

→

crude product

Rendimiento 87.0%

(S)-Indolin-2-ylmethanol

Rendimiento 87.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction mixture was heated
2. 2
   Temperaturato reflux for 12 h
3. 3
   OtroThe mixture was quenched with methanol (7.5 ml) and conc. HCl (2.5 ml)
4. 4
   Temperaturawith cooling
5. 5
   Temperaturawas then refluxed for additional 2 h
6. 6
   OtroThe solvent was evaporated
7. 7
   Extracciónextracted with dichloromethane
8. 8
   LavadoThe organic layer was washed with brine
9. 9
   Secadodried over sodium sulfate
10. 10
    Otrothe solvent was evaporated under reduced pressure

Procedimiento

To a solution of (S)-indoline-2-carboxylic acid (9.2 mmol, 1.0 equiv.) in THF (18 ml) was added dropwise BH3-DMS solution (18.4 mmol, 2 equiv.) and the reaction mixture was heated to reflux for 12 h. The mixture was quenched with methanol (7.5 ml) and conc. HCl (2.5 ml) with cooling and was then refluxed for additional 2 h. The solvent was evaporated and the residue was basified with 40% NaOH solution and extracted with dichloromethane. The organic layer was washed with brine, dried over sodium sulfate and the solvent was evaporated under reduced pressure to give the crude product which was purified by silica gel column chromatography. Yield: 87%.

Fuente