Reaktion #48687

Reaktionsgleichung

sodium borohydride

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

water

→

title compound

Ausbeute 78.7%

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

Ausbeute 78.7%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrate
2. 2
   workup.ADDITIONDilute with ethyl acetate (˜75 mL)
3. 3
   Filtrationfilter through Celite®
4. 4
   Waschenwash with 10% aqueous potassium carbonate, saturated aqueous sodium chloride
5. 5
   TrocknenDry (magnesium sulfate)
6. 6
   Filtrationfilter
7. 7
   Einengenconcentrate

Vorschrift

Add sodium borohydride (0.86 g, 22.60 mmol) to (2R,5R)-5-[(1R,2S)-3-(3,5-difluorophenyl)-1-hydroxy-2-nitropropyl]-2-(2,2-dimethylpropoxy)-morpholine-4-carboxylic acid tert-butyl ester (2.30 g, 4.71 mmol) and nickel (II) chloride (1.34 g, 10.36 mmol) in methanol (47 mL) at room temperature over 2 minutes. Stir for 20 minutes, add water (˜3 mL) and concentrate. Dilute with ethyl acetate (˜75 mL), filter through Celite®, wash with 10% aqueous potassium carbonate, saturated aqueous sodium chloride, Dry (magnesium sulfate), filter and concentrate to give the title compound as an off-white solid (1.7 g, 78.7%).

Quelle