Reaktion #48670

Reaktionsgleichung

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

sodium borohydride

water

→

desired compound

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

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrate
2. 2
   workup.ADDITIONDilute with ethyl acetate
3. 3
   Filtrationfilter through Celite®
4. 4
   SonstigePartition the filtrate between ethyl acetate and water
5. 5
   TrocknenDry the ethyl acetate layer (magnesium sulfate)
6. 6
   Filtrationfilter
7. 7
   Einengenconcentrate

Vorschrift

To a solution of (R)-5-[(1R,2S)-3-(3,5-difluorophenyl)-1-hydroxy-2-nitropropyl]-2-ethoxymorpholine-4-carboxylic acid tert-butyl ester (0.145 g, 0.325 mmol) in methanol (5 mL) at room temperature add nickel (II) chloride (0.063 g, 0.487 mmol) and then sodium borohydride (0.061 g, 1.62 mmol) portionwise. Stir 30 minutes, add water (˜3 mL) and concentrate. Dilute with ethyl acetate and filter through Celite®. Partition the filtrate between ethyl acetate and water. Dry the ethyl acetate layer (magnesium sulfate), filter and concentrate to give the desired compound as a white solid.

Quelle