Water → HCID 131717361, compound

Participants

Reaction Steps

4N aqueous sodium hydroxide (500 cc) is added slowly and with stirring to a suspension of (3aRS,7aRS)-7,7-diphenylperhydro-4-isoindolone hydrochloride (200 g) in ethyl acetate (2000 cc); stirring is continued until the starting material has disappeared. The organic solution is washed with distilled water (250 cc) and with saturated aqueous sodium chloride solution (250 cc), dried over magnesium sulphate and filtered. To the solution thereby obtained, a solution of L(+)-mandelic acid (92.8 g) in ethyl acetate (1000 cc) is added with stirring; after 4 hours' stirring, the crystals obtained are drained, crystals are taken up with distilled water (2000 cc); the mixture is heated to reflux with stirring for 15 minutes; the insoluble crystals are drained, washed with distilled water (2×100 cc) and dried. They are recrystallized in a mixture of acetonitrile (1100 cc) and distilled water (500 cc); the crystals obtained are drained, washed with acetonitrile (3×40 cc) and dried. (3aR,7aR)-7,7-Diphenylperhydro-4-isoindolone L-mandelate (80 g) is obtained; [α]D20 =-164° (c=1, methanol).

Provenance & Evidence