Reaktion #337028

Reaktionsgleichung

ethyl chloroacetate

(S)-2-amino-3-methylbutan-1-ol

sodium hydride

ammonium chloride

→

(S)-5-isopropylmorpholin-3-one

Ausbeute 67.0%

Lösungsmittel

toluene

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Temperaturat reflux for 20 h
3. 3
   Temperaturcooled to room temperature
4. 4
   workup.STIRRINGThe mixture was stirred for 20 min
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe crude material was purified by column chromatography (silica gel, 95:5 CH2Cl2/CH3OH)

Vorschrift

To an ice cold, stirred suspension of sodium hydride (60% in oil, 1.3 g, 34.0 mmol) in toluene (45 mL) was added dropwise a solution of (S)-2-amino-3-methylbutan-1-ol (1.5 g, 15.0 mmol) in toluene (30 mL). After the addition was complete, the reaction mixture was warmed to room temperature and a solution of ethyl chloroacetate (2.0 g, 16.0 mmol) in toluene (8 mL) was added in a dropwise manner. The resulting mixture was then stirred at reflux for 20 h, cooled to room temperature, and solid ammonium chloride (1.8 g, 34.0 mmol) added to the reaction. The mixture was stirred for 20 min and then concentrated under reduced pressure. The crude material was purified by column chromatography (silica gel, 95:5 CH2Cl2/CH3OH) to give (S)-5-isopropylmorpholin-3-one (1.4 g, 67%) as a light yellow solid. 1H NMR and MS consistent.

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