Potassium Carbonate → (3aRS,7aRS)-2-benzyl-7,7-dimethyl-4-perhydroisoindolone

Participants

Reaction Steps

To a solution of 5 g of 4,4-dimethylcyclohex-2-enone and 12.4 cm3 of N-butoxymethyl-N-trimethylsilylmethylbenzylamine in 100 cm3 of dichloromethane are added, at a temperature of 10° C., 5 drops of trifluoroacetic acid. The reaction mixture is stirred at this temperature for 3 hours, then 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 5.2 cm, height 25 cm), eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (85/15 by volume) and collecting 100 cm3 fractions. Fractions 39 to 63 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 3.64 g of (3aRS,7aRS)-2-benzyl-7,7-dimethyl-4-perhydroisoindolone are obtained in the form of a yellow oil.

Provenance & Evidence