反应详情

To a suspension of 27.6 g of 2-methoxyphenylmagnesium bromide in 60 cm' of tetrahydrofuran are added dropwise, at room temperature and with stirring, a solution of 4.7 g of (3aRS,5RS,7aSR)-5-acetoxy-2-benzyl-4-perhydroisoindolone in 90 cm3 of tetrahydrofuran. The reaction mixture is stirred at room temperature for 3 hours, treated with 200 cm3 of saturated aqueous ammonium chloride solution and taken up in 200 cm3 of ethyl ether and 100 g of ice. The organic phase is separated out after settling has taken place, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized in 80 cm3 of petroleum ether and then chromatographed on a column of silica gel (particle size 0.04-0.06 mm, diameter 1 cm, height 20 cm), eluting under a pressure of 0.5 bar of nitrogen with a mixture of dichloromethane and methanol (95/5 by volume) and collecting 25 cm3 fractions. Fractions 14 to 21 are combined and then concentrated to dryness under reduced pressure (2.5 kPa). 1.55 g of (3aRS,4RS,5RS,7aSR)-2-benzyl-4-(2-methoxyphenyl)-4,5-perhydroisoindolediol are obtained, melting at 140° C.

1. additionare added dropwise, at room temperature
2. stirringThe reaction mixture is stirred at room temperature for 3 hours
3. customThe organic phase is separated out after settling
4. dry with materialdried over magnesium sulphate
5. filtrationfiltered
6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
7. customThe residue is crystallized in 80 cm3 of petroleum ether
8. customchromatographed on a column of silica gel (particle size 0.04-0.06 mm, diameter 1 cm, height 20 cm)
9. washeluting under a pressure of 0.5 bar of nitrogen with a mixture of dichloromethane and methanol (95/5 by volume)
10. customcollecting 25 cm3 fractions
11. concentrationconcentrated to dryness under reduced pressure (2.5 kPa)