Phenylacetyl chloride → (3aR,7aR)-7,7-Diphenyl-2-(phenylacetyl)perhydro-4-isoindolone

Participants

Reaction Steps

A solution of phenylacetyl chloride (4 cc) and triethylamine (8.6 cc) in dichloromethane (10 cc) is added dropwise to a solution, cooled to +5° C., of (3aR,7aR)-7,7-diphenylperhydro-4-isoindolone hydrochloride (10 g) in dry dichloromethane (80 cc). The reaction mixture is stirred for 2 hours at +5° C. and then for 20 hours at 20° C. The reaction mixture is treated with saturated aqueous sodium hydrogen carbonate solution (30 cc); the organic phase is washed with distilled water (2×50 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized in acetonitrile (15 cc). The crystals are drained, washed with acetonitrile (10 cc) and with isopropyl ether (10 cc) and dried. (3aR,7aR)-7,7-Diphenyl-2-(phenylacetyl)perhydro-4-isoindolone (5.7 g), m.p. 173° C. is obtained; [α]D20 =-282° (c=1, methanol).

Provenance & Evidence