Reaktion #48611

Reaktionsgleichung

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

sodium borohydride

water

→

desired compound

Ausbeute 95.0%

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

Ausbeute 95.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenConcentrate
2. 2
   workup.DISSOLUTIONdissolve the residue in ethyl acetate
3. 3
   FiltrationFilter the black solution through a pad of Celite®
4. 4
   Waschenwash the filter cake with ethyl acetate
5. 5
   WaschenWash the filtrate with water (twice), saturated aqueous sodium chloride
6. 6
   Trocknendry (magnesium sulfate)
7. 7
   Filtrationfilter
8. 8
   Einengenconcentrate

Vorschrift

Combine (R)-4-[(1R,2S)-3-(3,5-difluorophenyl)-1-hydroxy-2-nitropropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (1.13 g, 2.71 mmol) and nickel (II) chloride (0.58 g, 4.485 mmol) in dry methanol (30 ml) and add sodium borohydride (0.454 g, 12 mmol) over 1 minute. Stir the resulting mixture for 20 minutes and then add water (3 mL). Concentrate and dissolve the residue in ethyl acetate. Filter the black solution through a pad of Celite® and wash the filter cake with ethyl acetate. Wash the filtrate with water (twice), saturated aqueous sodium chloride, dry (magnesium sulfate), filter, and concentrate to give the desired compound as a white solid (920 mg, 95%).

Quelle