Reaktion #828876

Reaktionsgleichung

product

(Z)-3-(3-[4,5-dihydro-5-(4-fluorophenyl)isoxazol-3-yl]phenyl)-2-propen-1-ol

PPh3

N,O-di-tert-butoxycarbonylhydroxylamine

diethylazodicarboxylate

→

title compound ( 16 )

Ausbeute 98.0%

(Z)-N,O-di-tert-butoxycarbonyl-N-[3-(3-[4,5-dihydro-5-(4-fluorophenyl)isoxazol-3-yl]phenyl)-2-propen-1-yl]-N-hydroxylamine

Ausbeute 98.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigesolvent was removed under reduced pressure
2. 2
   SonstigeThe resultant residue was purified by column chromatography on silica gel (eluent=ethyl acetate:n-hexane, 1:7)

Vorschrift

To a solution of the product of Step 3, above (15, 1.8 g, 6 mmol), PPh3 (1.9 g, 7.2 mmol) and N,O-di-tert-butoxycarbonylhydroxylamine (1.85 g, 7.8 mmol) in THF (25 ml) was added dropwise a solution of diethylazodicarboxylate (1.2 ml, 7.2 mmol) in THF (5 ml) under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 1.5 hours and solvent was removed under reduced pressure. The resultant residue was purified by column chromatography on silica gel (eluent=ethyl acetate:n-hexane, 1:7) to afford 3.0 g (98% yield) of the title compound (16) as a colorless oil.

Quelle