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

HRID 619107Notes

Reaction equation

HRID 619107 reaction equation
[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]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 109925342-[4-(2,3-Dihydro[1,4]benzodioxin-5-yl)piperazin-1-yl]-6-methoxyindan-1-one

Product 1

HCID 15860117Cis-2-[4-(2,3-dihydro[1,4]benzodioxin-5-yl)piperazin-1-yl]-6-methoxyindan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  1. temperaturefor 4 hours at reflux
  2. customAfter evaporation
  3. washwashed twice with 500 ml of water
  4. dry with materialdried over magnesium sulphate
  5. concentrationAfter concentration
  6. customthe residue is chromatographed over silica (eluant
  7. washThe product eluted first corresponds to the cis isomer

Sources & evidence

ORD record
ord-ea098ba1a3ec440d8fce91cda283a8ae
Source dataset
uspto-grants-1999_09
Patent number
US05958927

Reaction notes

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