Water → HCID 67719131, compound

Participants

Reaction Steps

To a solution of 1 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[(4-nitrophenyl)acetyl]perhydro-4,5-isoindolediol in 3.3 cm3 of methanol, maintained at a temperature of 50° C., are added 33 cm3 of water, 4.6 g of ammonium chloride and 2.2 g of zinc powder. The reaction mixture is brought to reflux for 30 minutes, cooled to room temperature and then washed with twice 50 cm3 of dichloromethane. The organic phase is separated off after settling, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is taken up in 70 cm3 of 1N hydrochloric acid. The organic phase is extracted with twice 50 cm3 of ethyl acetate. The aqueous phase is basified with 1N sodium hydroxide and the organic phase is then extracted with 3 times 100 cm3 of ethyl acetate. It is separated off after settling, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The meringue-like product obtained is crystallized in 20 cm3 of isopropyl ether. 0.71 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[(4-aminophenyl)acetyl]perhydro-4,5-isoindolediol is obtained, melting at 188° C.

Provenance & Evidence