Réaction #11701

Équation de réaction

sodium triacetoxyborohydride

sodium hydroxide

(S)-2-amino-propionic acid methyl ester hydrochloride

4-fluorobenzaldehyde

triethylamine

→

title compound

Rendement 91.0%

(S)-2-(4-Fluoro-benzylamino)-propionic acid methyl ester

Rendement 91.0%

Solvants

1,2-dichloroethane

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe resulting mixture was stirred overnight at ambient temperature
2. 2
   Extractionextracted with dichloromethane
3. 3
   SéchageThe organic layer was dried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo

Mode opératoire

To a solution of (S)-2-amino-propionic acid methyl ester hydrochloride (25 g, 179 mmol) and 4-fluorobenzaldehyde (23 mL, 215 mmol) in 1,2-dichloroethane (200 mL) was added triethylamine (25 mL, 179 mmol). The resulting mixture was stirred for two hours at ambient temperature followed by addition of sodium triacetoxyborohydride (57 g, 268 mmol) in four portions. The resulting mixture was stirred overnight at ambient temperature. The reaction was neutralized with dilute aqueous sodium hydroxide solution and extracted with dichloromethane. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the title compound (34.4 g).

Source