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

Participants

Reaction Steps

To a solution of 1 g of 6-methyl-cyclohex-2-enone in 15 cm3 of dichloromethane are added, at room temperature, 3 drops of trifluoroacetic acid, followed by 3.6 cm3 of N-butoxymethyl-N-trimethylsilylmethylbenzylamine. The reaction mixture is brought to reflux, with stirring, for 3 hours. After cooling, potassium carbonate is 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 2 cm, height 20 cm), eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (60/40 by volume) and collecting 25 cm3 fractions. Fractions 10 to 20 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 0.7 g of (3aRS,5RS,7aSR)-2benzyl-5-methyl-4-perhydroisoindolone is obtained in the form of a colourless oil.

Provenance & Evidence