تفاعل #48699

معادلة التفاعل

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

المردود 87.0%

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

المردود 87.0%

المذيبات

ethyl acetate

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةHeat
2. 2
   درجة الحرارةto reflux for 16 hours
3. 3
   غسيلWash with ammonium chloride (1.5 L), saturated aqueous sodium chloride (1.5 L)
4. 4
   تجفيفdry (magnesium sulfate)
5. 5
   ترشيحfilter
6. 6
   تركيزconcentrate
7. 7
   أخرىpurify
8. 8
   غسيل(silica gel chromatography, eluting with 5:95 to 20:80 ethyl acetate:hexanes)

الإجراء التجريبي

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%).

المصدر