Potassium Carbonate → (3aRS,6SR,7aSR)-6-acetoxymethyl-2-benzyl-4-perhydroisoindolone

Participants

Reaction Steps

Two drops of trifluoroacetic acid are added to a solution of 6.5 g of 5-acetoxymethylcyclohex-2-en-1-one and 14 g of N-butoxymethyl-N-trimethylsilylmethylbenzylamine [prepared according to the method described by Y. Tarao et al., Chem. Pharm. Bull., 33., 2762 (1985)] in 60 cm3 of dry dichloromethane. On reaching reflux, the reaction mixture is maintained at the same temperature for 30 minutes and then left at 20° C. for one hour. After addition of 1.0 g of potassium carbonate, the suspension obtained is filtered, and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The oily residue obtained is chromatographed on a silica gel column (particle size 0.06-0.2 mm, height 42 cm) in a mixture of cyclohexane and ethyl acetate (40:60 by volume) and then in ethyl acetate. 8.2 g of (3aRS,6SR,7aSR)-6-acetoxymethyl-2-benzylperhydroisoindol-4-one are obtained in the form of a yellowish oil.

Provenance & Evidence