Phenylacetic Acid → (3aRS,7aRS)-7,7-diphenyl-2-(phenylacetyl)-4-perhydroisoindolone

Participants

Reaction Steps

N,N'-Carbonyldiimidazole (1.7 g) is added to a solution of phenylacetic acid (1.34 g) in dry dichloromethane (30 cc) cooled to +5° C. The mixture is stirred for 1 hour at +5° C. and a solution of 7,7-diphenyl-4-perhydroisoindolone hydrochloride (3.27 g) and triethylamine (1.7 cc) in dichloromethane (30 cc) is then added. The reaction mixture is stirred for 1 hour at +5° C. and then for 1 hour at 20° C. The reaction mixture is washed with a saturated aqueous solution (50 cc) of sodium bicarbonate, dried over magnesium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized from acetonitrile (15 cc). The crystals are drained, washed with isopropyl ether (10 cc) and dried. (3aRS,7aRS)-7,7-diphenyl-2-(phenylacetyl)-4-perhydroisoindolone (2.7 g) melting at 216° C. is obtained.

Provenance & Evidence