Potassium Carbonate → HCID 67915812, compound

Participants

Reaction Steps

Trifluoroacetic acid (12 drops) is added to a solution of 4,4-bis(3-tolyl)cyclohexenone (16.7 g) and N-butoxymethyl-N-(trimethylsilylmethyl)benzylamine (18.7 cc) in dry dichloromethane (150 cc). The reaction mixture is brought to reflux, then stirred for 3 hours while allowing the temperature the return to 25° C. and for a further 10 minutes after the addition of potassium carbonate (12 g). After filtration and concentration to dryness under reduced pressure (2.7 kPa), the residue is chromatographed on a column of silica gel (particle size 0.04-0.063 mm, diameter 5 cm, height 50 cm), eluting under a nitrogen pressure of 0.7 bar with a mixture of cyclohexane and ethyl acetate (85:15) and collecting 25-cc fractions. Fractions 14 to 30 are combined and concentrated to dryness under reduced pressure (2.7 kPa) to give (3aRS,7aRS)-2-benzyl-7,7-bis(3-tolyl)perhydro-4-isoindolone (13.9 g) in the form of a colorless oil.

Provenance & Evidence