Reaktion #74269

Reaktionsgleichung

(S)-indoline-2-carboxylic acid

→

crude product

Ausbeute 87.0%

(S)-Indolin-2-ylmethanol

Ausbeute 87.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was heated
2. 2
   Temperaturto reflux for 12 h
3. 3
   SonstigeThe mixture was quenched with methanol (7.5 ml) and conc. HCl (2.5 ml)
4. 4
   Temperaturwith cooling
5. 5
   Temperaturwas then refluxed for additional 2 h
6. 6
   SonstigeThe solvent was evaporated
7. 7
   Extraktionextracted with dichloromethane
8. 8
   WaschenThe organic layer was washed with brine
9. 9
   Trocknendried over sodium sulfate
10. 10
    Sonstigethe solvent was evaporated under reduced pressure

Vorschrift

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%.

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