Potassium Carbonate → HCID 67915832, compound

Participants

Reaction Steps

Trifluoroacetic acid (15 drops) is added to a solution of 4,4-bis(3-chlorophenyl)cyclohexenone (26.8 g) and N-butoxymethyl-N-(trimethylsilylmethyl)benzylamine (33 cc) in dry dichloromethane (200 cc). The reaction mixture is brought to reflux, then stirred for 16 hours after the temperature has been allowed to return to 25° C. and for a further 15 minutes after the addition of potassium carbonate (16 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 0.04-00063 mm, diameter 7 cm, height 40 cm), eluting under a nitrogen pressure of 0.5 bar with a mixture of cyclohexane and ethyl acetate (75:25) and collecting 500-cc fractions. Fractions 12 to 18 are combined and concentrated to dryness under reduced pressure (2.7 kPa) to give (3aRS,7aRS)-2-benzyl-7,7-bis(3-chlorophenyl)perhydro-4-isoindolone (16.2 g) in the form of a yellow oil.

Provenance & Evidence