Reaktion #48741

Reaktionsgleichung

2-ethoxyphenylboronic acid

sodium carbonate

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

→

title compound

Ausbeute 46.4%

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

Ausbeute 46.4%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeflushed with nitrogen
2. 2
   ExtraktionAdd saturated aqueous sodium chloride and extract with ethyl acetate (2×50 mL)
3. 3
   TrocknenDry over magnesium sulfate
4. 4
   Einengenconcentrate under reduced pressure
5. 5
   Wascheneluting with hexanes containing 25-50% ethyl acetate

Vorschrift

Add 2-ethoxyphenylboronic acid (0.065 g, 0.394 mmol) and (1,1′-bis(diphenylphosphino)ferrocene) palladium(II) chloride (0.021 g) to a mixture of 2M sodium carbonate solution (0.262 g, 0.525 mmol) and (2R,3S,5R)-5-[(1S,2S)-1-hydroxy-2-acetylamino-3-(3-bromo-5-fluorophenyl)-propyl]-2-(2,2-dimethylpropoxy)-3-methylmorpholine-4-carboxylic acid tert-butyl ester (0.151 g, 0.262 mmol) in tetrahydrofuran (2.62 mL) in a sealed tube flushed with nitrogen. Heat the tube at 80° C. for 3 days. Add saturated aqueous sodium chloride and extract with ethyl acetate (2×50 mL). Dry over magnesium sulfate and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with hexanes containing 25-50% ethyl acetate to provide the title compound (0.075 g, 46%) as a white foam.

Quelle