Triethylamine → (3aR, 7aR)-2-[(RS)-2-(2-dimethylaminophenyl)propionyl]-7,7-diphenylperhydro-4-isoindolone

Participants

Reaction Conditions

Reaction Steps

N,N'-Carbonyldiimidazole (0.85 g) is added to a solution of (RS)-2-[2-dimethylaminophenyl]propionic acid (1 g) in dichloromethane (30 cc) cooled to 5° C. and the mixture is then stirred for 30 minutes at this temperature. A solution of (3aR,7aR)-7,7-diphenyl-4-perhydroisoindolone hydrochloride (1.7 g) and triethylamine (1.4 cc) in dichloromethane (30 cc) is added. The reaction mixture is stirred at 20° C. for 16 hours, washed with water (2×100 cc), dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (0.2-0.063 mm, diameter 3 cm, height 50 cm), eluting under a nitrogen pressure of 0.5 bar with ethyl acetate and collecting 125 cc fractions. Fractions 4 to 6 are combined and concentrated to dryness under reduced pressure (2.7 kPa) to give (3aR,7aR)-2-[(RS)-2-(2 -dimethylaminophenyl)propionyl]-7,7-diphenyl-4-perhydroisoindolone (1.4 g) in the form of a white meringue.

Provenance & Evidence