Sodium borohydride → Cis-2-[4-(2,3-dihydro[1,4]benzodioxin-5-yl)piperazin-1-yl]-6-methoxyindan-1-ol
Reaktionsgleichung
[BH4-].[Na+].[O:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([N:13]3[CH2:18][CH2:17][N:16]([CH:19]4[CH2:27][C:26]5[C:21](=[CH:22][C:23]([O:28][CH3:29])=[CH:24][CH:25]=5)[C:20]4=[O:30])[CH2:15][CH2:14]3)[C:7]=2[O:6][CH2:5][CH2:4]1>O1CCCC1>[O:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([N:13]3[CH2:14][CH2:15][N:16]([C@H:19]4[CH2:27][C:26]5[C:21](=[CH:22][C:23]([O:28][CH3:29])=[CH:24][CH:25]=5)[C@H:20]4[OH:30])[CH2:17][CH2:18]3)[C:7]=2[O:6][CH2:5][CH2:4]1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
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 litre 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 el al. (Justus Liebigs Ann. Chem., 1969, 726, 25-29).