Diisopropyl Ether → (3aRS,7aRS)-7,7-Diphenyl-2-vinyloxycarbonylperhydro-4-isoindolone

Participants

Reaction Steps

Vinyl chloroformate (56 cc) is added dropwise in the course of 10 minutes to a solution of (3aRS,7aRS)-2-benzyl-7,7-diphenyl-4-perhydroisoindolone (193 g) in 1,2-dichloroethane (1,225 cc) cooled to +5° C. After stirring for 30 minutes at between 10° and 20° C., the reaction mixture is refluxed for 90 minutes, cooled and concentrated to dryness under reduced pressure (2.7 kPa then 1 kPa). The crystalline mass obtained is pounded with cold isopropyl ether (200 cc). The crystals obtained are drained, washed with isopropyl ether (2 * 100 cc) and dried. (3aRS,7aRS)-7,7-diphenyl-2-vinyloxycarbonyl-4-perhydroisoindolone (177 g) melting at 178° C. is obtained.

Provenance & Evidence