C([O:4][CH2:5][CH:6]1[CH2:14][CH:13]2[CH:9]([CH2:10][N:11]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12]2)[C:8](=[O:22])[CH2:7]1)(=O)C.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[Mg]Br.[Cl-].[NH4+].C(OCC)(=O)C>O1CCCC1>[CH2:15]([N:11]1[CH2:10][CH:9]2[CH:13]([CH2:14][CH:6]([CH2:5][OH:4])[CH2:7][C:8]2([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[O:24][CH3:23])[OH:22])[CH2:12]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1A solution of 8.0 g of (3aRS,6SR,7aSR)-6-acetoxymethyl-2-benzylperhydroisoindol-4-one in 60 cm3 of anhydrous tetrahydrofuran is added to a suspension of 2-methoxyphenylmagnesium bromide (prepared from 24.9 cm3 of 2-bromoanisole and 4.86 g of magnesium) in 200 cm3 of anhydrous tetrahydrofuran. The reaction mixture is stirred at 20° C. for 20 hours, then cooled to +5° C. and treated with 120 cm3 of saturated aqueous ammonium chloride solution and 100 cm3 of ethyl acetate. After filtration of the mixture, the organic phase is washed with brine, then dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (particle size 0.06-0.20 mm, height 40 cm) in a mixture of 1,2-dichloroethane and methanol (95:5 by volume). Recrystallization from ethyl ether gives 3.2 g of (3aRS,4RS,6SR,7aSR)-2-benzyl-6-hydroxymethyl-4-(2-methoxyphenyl)perhydroisoindol-4-ol in the form of a white solid melting at 110° C.
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