Sodium borohydride → Cis-2-[4-(2,3-dihydro[1,4]benzodioxin-5-yl)piperazin-1-yl]-6-methoxyindan-1-ol

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Reaction Steps

2.8 g (73.8 mmol) of sodium borohydride are added in fractions over the course of 15 minutes at room temperature to 28.0 g (73.6 mmol) of the compound obtained in Step 2 in 220 ml of tetrahydrofuran. The mixture is stirred overnight at room temperature, and then for 4 hours at reflux. After evaporation, the residue is taken up in 1 liter of dichloromethane, washed twice with 500 ml of water and then dried over magnesium sulphate. After concentration, the residue is chromatographed over silica (eluant: dichloromethane/methanol 99/1, then 98/2). The product eluted first corresponds to the cis isomer. Its stereochemistry was demonstrated by IR, in solution in chloroform, according to the method described by H. -J. Rimek et al. (Justus Liebigs Ann. Chem., 1969, 726, 25-29).

Provenance & Evidence