반응 #11701

반응 방정식

sodium triacetoxyborohydride

sodium hydroxide

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

4-fluorobenzaldehyde

triethylamine

→

title compound

수율 91.0%

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

수율 91.0%

용매

1,2-dichloroethane

반응 조건

후처리

1. 1
   workup.STIRRINGThe resulting mixture was stirred overnight at ambient temperature
2. 2
   추출extracted with dichloromethane
3. 3
   건조The organic layer was dried over magnesium sulfate
4. 4
   여과filtered
5. 5
   농축concentrated in vacuo

실험 절차

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).

출처