Reaktion #48738

Reaktionsgleichung

(2R,3S,5R)-5-[(1R,2S)-3-(3-bromo-5-fluoro-phenyl)-1-hydroxy-2-nitro-propyl]-2-(2,2-dimethyl-propoxy)-3-methyl-morpholine-4-carboxylic acid tert-butyl ester

→

title compound

Ausbeute 99.5%

(2R,3S,5R)-5-[(1S,2S)-1-Hydroxy-2-amino-3-(3-bromo-5-fluorophenyl)-propyl]-2-(2,2-dimethylpropoxy)-3-methylmorpholine-4-carboxylic acid tert-butyl ester

Ausbeute 99.5%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationFilter the reaction mixture
2. 2
   Waschenwash the filter cake with cold water (100 mL)
3. 3
   ExtraktionExtract the neutralized aqueous phase with ethyl acetate (3×250 mL)
4. 4
   TrocknenDry the combined organic phases with magnesium sulfate
5. 5
   Einengenconcentrate under reduced pressure

Vorschrift

Add zinc (0.604 g, 9.23 mmol) to a solution of (2R,3S,5R)-5-[(1R,2S)-3-(3-bromo-5-fluoro-phenyl)-1-hydroxy-2-nitro-propyl]-2-(2,2-dimethyl-propoxy)-3-methyl-morpholine-4-carboxylic acid tert-butyl ester (0.520 g, 0.923 mmol) in acetic acid (9.23 mL). Stir the reaction mixture for 22 hours at room temperature. Filter the reaction mixture and wash the filter cake with cold water (100 mL). Add saturated aqueous sodium bicarbonate to the filtrate to neutralize the acid. Extract the neutralized aqueous phase with ethyl acetate (3×250 mL). Dry the combined organic phases with magnesium sulfate and concentrate under reduced pressure to provide the title compound (0.49 g, 99.5%) as a white foam.

Quelle