Reaktion #48739

Reaktionsgleichung

propyl zinc bromide

(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 60.0%

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

Ausbeute 60.0%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeflushed with nitrogen
2. 2
   ExtraktionExtract the reaction mixture with ethyl acetate (2×30 mL)
3. 3
   WaschenCombine the organic phases and wash with saturated aqueous sodium chloride (1×15 mL)
4. 4
   Trocknendry over magnesium sulfate
5. 5
   Einengenconcentrate under reduced pressure
6. 6
   WaschenSubject residue to silica gel chromatography, eluting with hexanes containing 15-45% ethyl acetate

Vorschrift

Add propyl zinc bromide (2.311 g) in tetrahydrofuran and (1,1′-bis(diphenylphosphino)ferrocene) palladium(II) chloride (0.015 g) to a solution of (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 (0.07 g, 0.122 mmol) in tetrahydrofuran (1.2 mL) in a sealed tube flushed with nitrogen. Heat the tube at 65° C. for 6.5 hours. Add saturated aqueous ammonium chloride (5 mL). Extract the reaction mixture with ethyl acetate (2×30 mL). Combine the organic phases and wash with saturated aqueous sodium chloride (1×15 mL), dry over magnesium sulfate and concentrate under reduced pressure. Subject residue to silica gel chromatography, eluting with hexanes containing 15-45% ethyl acetate, to provide 0.039 g (60%) of the title compound as an off-white foam.

Quelle