Diethyl Ether → 2-Benzyl-7,7-diphenyl-4-(2-methoxyphenyl)perhydro-4,5-isoindolediol

関与物質

反応手順

To a suspension of 84.4 g of 2-methoxyphenylmagnesium bromide in 1000 cm3 of tetrahydrofuran is added dropwise, at room temperature and with stirring, a solution of 22 g of (3aRS,5RS,7aRS)-5-acetoxy-2-benzyl-7,7-diphenylperhydro-4-isoindolone in 220 cm3 of tetrahydrofuran. The reaction mixture is stirred at room temperature for 18 hours, treated with 200 cm3 of saturated aqueous ammonium chloride solution, and taken up with 200 cm3 of diethyl ether and 200 g of ice. 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 crystallized in 250 cm3 of petroleum ether and then recrystallized in 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)perhydro-4,5-isoindolediol are obtained, melting at 236° C.

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