Reaktion #48699

Reaktionsgleichung

benzyl bromide

potassium carbonate

(R)-4-[(1S,2S)-2-amino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

→

desired compound

Ausbeute 87.0%

(R)-4-[(1S,2S)-2-Dibenzylamino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

Ausbeute 87.0%

Lösungsmittel

ethyl acetate

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturHeat
2. 2
   Temperaturto reflux for 16 hours
3. 3
   WaschenWash with ammonium chloride (1.5 L), saturated aqueous sodium chloride (1.5 L)
4. 4
   Trocknendry (magnesium sulfate)
5. 5
   Filtrationfilter
6. 6
   Einengenconcentrate
7. 7
   Sonstigepurify
8. 8
   Waschen(silica gel chromatography, eluting with 5:95 to 20:80 ethyl acetate:hexanes)

Vorschrift

Add benzyl bromide (75 mL, 630.55 mmol) to a suspension of potassium carbonate (85 g, 615.006 mmol) and (R)-4-[(1S,2S)-2-amino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (80 g, 207.25 mmol) in acetonitrile (900 mL). Heat to reflux for 16 hours, cool to room temperature, and dilute with ethyl acetate (2 L). Wash with ammonium chloride (1.5 L), saturated aqueous sodium chloride (1.5 L), dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 5:95 to 20:80 ethyl acetate:hexanes) to give the desired compound as a white solid (102.1 g, 87%).

Quelle