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-trimethylsilylmethylbenzylamine (33 cc) in dry dichloromethane (200 cc). The reaction mixture is brought to reflux and then stirred for 16 hours after having allowed the temperature to return to 25° C. and for a further 15 minutes after addition of potassium carbonate (16 g). After filtering and concentrating the filtrate to dryness under reduced pressure (2.7 kPa), the residue is chromatographed on a silica gel column (particle size 0.04-0.063 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 by volume) 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)-4-perhydroisoindolone (16.2 g) in the form of a yellow oil.

Provenance & Evidence