Reaktion #48613

Reaktionsgleichung

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

sodium iodide

benzyl bromide

→

desired compound

Ausbeute 85.4%

(R)-4-[(1S,2S)-2-Acetylamino-1-benzyloxy-3-(3,5-difluoro-phenyl)-propyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

Ausbeute 85.4%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGStir the resulting mixture for 2.5 hours
2. 2
   Sonstigequench by the addition of a 1:1 mixture of saturated aqueous ammonium chloride and saturated aqueous sodium chloride
3. 3
   workup.ADDITIONDilute the resulting mixture with ethyl acetate
4. 4
   WaschenWash the organic phase with saturated aqueous sodium chloride
5. 5
   Trocknendry over magnesium sulfate
6. 6
   Filtrationfilter
7. 7
   Einengenconcentrate
8. 8
   Sonstigepurify
9. 9
   Waschen(silica gel chromatography, eluting with 0:100 to 40:60 ethyl acetate:hexanes)

Vorschrift

Suspend (R)-4-[(1S,2S)-2-acetylamino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (4.78 g, 11.2 mmol) in dry tetrahydrofuran (115 ml) under a nitrogen atmosphere and add sodium hydride NaH (60% weight dispersion in mineral oil, 1.17 g, 29.3 mmol). Stir the resulting mixture for 30 minutes and then add sequentially sodium iodide (600 mg, 4.0 mmol) and benzyl bromide (2.7 mL, 22.7 mmol). Stir the resulting mixture for 2.5 hours and then quench by the addition of a 1:1 mixture of saturated aqueous ammonium chloride and saturated aqueous sodium chloride. Dilute the resulting mixture with ethyl acetate and discard the aqueous phase. Wash the organic phase with saturated aqueous sodium chloride, dry over magnesium sulfate, filter, concentrate and purify (silica gel chromatography, eluting with 0:100 to 40:60 ethyl acetate:hexanes) to give the desired compound as a white foam (4.96 g, 85%).

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