Triethylamine → HCID 67915957, compound

Participants

Reaction Steps

N,N'-Carbonyldiimidazole (1.13 g) is added to a solution of 2-[2-(1-pyrrolydinyl)phenyl]acetic acid (1.42 g) in dry dichloromethane (30 cc), cooled to +5° C. The mixture is stirred for 40 minutes at +5° C. and a solution of (3aRS,7aRS)-7,7-diphenyl-4-perhydroisoindolone hydrochloride (2.3 g) and triethylamine (0.98 cc) in dichloromethane (20 cc) is then added. The reaction mixture is stirred for 1 hour at +5° C. and then for 1 hour at 20° C. It is washed with distilled water (2×20 cc), dried over magnesium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (0.2-0.063 mm, diameter 2 cm, height 25 cm), eluting with a mixture of ethyl acetate and cyclohexane (70/30 by volume) and collecting 100 cc fractions. Fractions 3 to 8 are combined and concentrated to dryness under reduced pressure (2.7 kPa). The residue is recrystallized from a mixture of acetonitrile (5 cc) and isopropyl ether (5 cc). The crystals are drained, washed with ethylene oxide (10 cc) and dried. (3aRS,7aRS)-7,7-diphenyl-2-[2-[2-(1-pyrrolidinyl)phenyl]acetyl]-4-perhydroisoindolone (2.2 g) melting at 178° C. is obtained.

Provenance & Evidence