Reaktion #51225

Reaktionsgleichung

trans-4-(benzyloxycarbonylamino)cyclohexanecarbonyl chloride

tributylphenyltin

→

N-benzyloxycarbonyl-trans-4-benzoylcylohexylamine

Ausbeute 77.4%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Einengenthe reaction mixture was concentrated by a centrifugal concentrator
3. 3
   workup.DISSOLUTIONthe residue was dissolved in tetrahydrofuran
4. 4
   Sonstigeevaporated to dryness with 5 g of silica gel
5. 5
   SonstigeThe resulting residue was purified by silica gel flash chromatography (solvent

Vorschrift

Under argon atmosphere, a mixture comprising 1.0 g trans-4-(benzyloxycarbonylamino)cyclohexanecarbonyl chloride, 1.92 g of tributylphenyltin, 61 mg of dichlorobis(triphenylphosphine)palladium and 10 mL of dioxane was stirred at 110° C. for 12 hours. After cooling, the reaction mixture was concentrated by a centrifugal concentrator, and then, the residue was dissolved in tetrahydrofuran and evaporated to dryness with 5 g of silica gel. The resulting residue was purified by silica gel flash chromatography (solvent: ethyl acetate-hexane (1:2) to (1:1) to obtain 883 mg of N-benzyloxycarbonyl-trans-4-benzoylcylohexylamine.

Quelle