反応 #11701

反応方程式

sodium triacetoxyborohydride

sodium hydroxide

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

4-fluorobenzaldehyde

triethylamine

→

title compound

収率 91.0%

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

収率 91.0%

溶媒

1,2-dichloroethane

反応条件

後処理

1. 1
   workup.STIRRINGThe resulting mixture was stirred overnight at ambient temperature
2. 2
   抽出extracted with dichloromethane
3. 3
   乾燥The organic layer was dried over magnesium sulfate
4. 4
   ろ過filtered
5. 5
   濃縮concentrated in vacuo

実験手順

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).

出典