Reaktion #48640

Reaktionsgleichung

sodium borohydride

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

→

desired compound

Ausbeute 100.0%

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

Ausbeute 100.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstir for 15 minutes
2. 2
   ExtraktionAdd water (2 mL), 0.1 N sodium hydroxide (2 mL) and extract with ethyl acetate (2×30 mL)
3. 3
   WaschenCombine organic extracts, wash with saturated aqueous sodium chloride (30 mL)
4. 4
   Trocknendry (sodium sulfate)
5. 5
   Filtrationfilter through a pad of Celite®
6. 6
   Einengenconcentrate

Vorschrift

Dissolve (2R,5R)-5-[(1R,2S)-3-(3-chloro-5-fluorophenyl)-1-hydroxy-2-nitropropyl]-2-(2,2-dimethylpropoxy)-morpholine-4-carboxylic acid tert-butyl ester (0.455 g, 0.901 mmol) in methanol (8 mL) and stir at room temperature in an oil bath. Add anhydrous nickel (II) chloride (0.175 g, 1.35 mmol) followed by sodium borohydride (0.170 mg, 4.50 mmol) in 3 portions over 5 minutes and stir for 15 minutes. Add water (2 mL), 0.1 N sodium hydroxide (2 mL) and extract with ethyl acetate (2×30 mL). Combine organic extracts, wash with saturated aqueous sodium chloride (30 mL), dry (sodium sulfate), filter through a pad of Celite® and concentrate to give the desired compound as a colorless oil (0.428 g).

Quelle