Potassium Carbonate → HCID 22843225, compound

Participants

Reaction Steps

Triethyloxonium tetrafluoborate (6.34 g) is added to a stirred suspension of (RS)-2-(2-methoxyphenyl)propionamide (5.4 g) in anhydrous dichloromethane (60 cc). The reaction mixture is stirred for 20 hours. A solution of (3aR,7aR)-7,7-diphenyl-4-perhydroisoindolone hydrochloride (6.65 g) and triethylamine (2.8 cc) in dichloromethane (30 cc) is added. The reaction mixture is refluxed for 5 hours. It is then cooled to +5° C. and is then treated with a 10% aqueous potassium carbonate solution (20 cc). After filtering, the organic phase is washed with distilled water (20 cc), dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a neutral alumina column (0.05 mm-0.160 mm, diameter 5 cm, height 20 cm), eluting with a mixture of cyclohexane and ethyl acetate (50/50) and collecting 250 cc fractions. The first fraction is concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (0.04 mm-0.06 mm, diameter 2 cm, height 35 cm), eluting with a mixture of n-butanol/acetic acid/pyridine/water (90/4/4/2 by volume) and collecting 20 cc fractions. Fractions 14 to 19 are concentrated to dryness under reduced pressure (0.13 kPa). The residue is taken up in dichloromethane (40 cc) and washed with aqueous potassium carbonate solution (10 cc). The organic phase is dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized from diisopropyl ether. The crystals are drained and dried under reduced pressure (0.13 kPa). (3aR,7aR)-2-[1-imino-2-(2-methoxyphenyl)-2-methylethyl]-7,7-diphenyl-4-perhydroisoindolone, form A, (0.12 g) is obtained in the form of a white meringue.

Provenance & Evidence