Reaktion #462464

Reaktionsgleichung

1-(t-butylacetamido)-3-azido-5,7-diphenylhexahydroazepin-2-one

→

1-(t-Butylacetamido)-3-amino-5,7-diphenylhexahydroazepin-2-one

Lösungsmittel

methanol

ethanol

methylene chloride

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationIt was filtered through Celite with ethanol and methylene chloride
2. 2
   Sonstigeevaporated
3. 3
   Sonstigechromatographed on silica gel using 30% methanol in ethyl acetate as eluant
4. 4
   Sonstigeto afford 300 mg (29%) of the less polar diastereomer as an oil and 420 mg (41%) of the more polar diastereomer as an oil

Vorschrift

A solution of 1.09 g (2.60 mmol) 1-(t-butylacetamido)-3-azido-5,7-diphenylhexahydroazepin-2-one in 30 mL ethanol and 15 mL methylene chloride was hydrogenated at 42 psi in the presence of 0.40 g 10% palladium-on-carbon for 36 hours. The reaction showed Rf 0.30/0.15 iodoplatinate positive, in 30% methanol in ethyl acetate. It was filtered through Celite with ethanol and methylene chloride, evaporated, and chromatographed on silica gel using 30% methanol in ethyl acetate as eluant to afford 300 mg (29%) of the less polar diastereomer as an oil and 420 mg (41%) of the more polar diastereomer as an oil.

Quelle