Potassium Carbonate → (3aRS,5RS,7aSR)-5-acetoxy-2-benzyl-4-perhydroisoindolone

Beteiligte Stoffe

Reaktionsschritte

To a solution of 7.5 g of 6-acetoxy-2-cyclohexenone and 16.83 cm3 of N-butoxymethyl-N-trimethylsilylmethylbenzylamine in 150 cm3 of dichloromethane are added, at a temperature of 10° C., 12 drops of trifluoroacetic acid. The reaction mixture is stirred at room temperature for 7 hours, then 2 g of potassium carbonate are added and the solution is filtered through a sinter funnel and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel (particle size 0.04-0.06 mm, diameter 6 cm, height 35 cm), eluting under a pressure of 0.5 bar of nitrogen with a mixture of dichloromethane and methanol (97.5-2.5 by volume) and collecting 60 cm3 fractions. Fractions 25 to 39 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 6.25 g of (3aRS,5RS,7aSR)-5-acetoxy-2-benzyl-4-perhydroisoindolone are obtained in the form of a yellow oil.

Herkunft & Nachweise