Ammonium Chloride → 2-Benzyl-7,7-diphenyl-4-(2-methoxyphenyl)perhydro-4,5-isoindolediol

Participants

Reaction Steps

A solution of 22 g of (3aRS,5RS,7aRS)-5-acetoxy-2-benzyl-7,7-diphenylperhydroisoindol-4-one in 220 cm3 of tetrahydrofuran is added dropwise to a suspension of 84.4 g of 2-methoxyphenylmagnesium bromide in 1000 cm3 of tetrahydrofuran at room temperature, while stirring. The reaction mixture is stirred at room temperature for 18 hours, treated with 200 cm3 of an aqueous saturated solution of ammonium chloride and taken up in 200 cm3 of ethyl ether and 200 g of ice. The organic phase is separated by settling, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized from 250 cm3 of petroleum ether and then recrystallized from 200 cm3 of methanol; the crystals are washed with 200 cm3 of isopropyl ether. 16.4 g of (3aRS,4RS,5RS,7aRS)-2-benzyl- 7,7-diphenyl-4- (2-methoxyphenyl)perhydroisoindole-4,5-diol which melts at 236° C. are obtained.

Provenance & Evidence