반응 #48699

반응 방정식

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

수율 87.0%

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

수율 87.0%

용매

ethyl acetate

acetonitrile

반응 조건

후처리

1. 1
   온도Heat
2. 2
   온도to reflux for 16 hours
3. 3
   세척Wash with ammonium chloride (1.5 L), saturated aqueous sodium chloride (1.5 L)
4. 4
   건조dry (magnesium sulfate)
5. 5
   여과filter
6. 6
   농축concentrate
7. 7
   기타purify
8. 8
   세척(silica gel chromatography, eluting with 5:95 to 20:80 ethyl acetate:hexanes)

실험 절차

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%).

출처