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

HRID 1107420Notes

Reaction equation

HRID 1107420 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 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).

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-4fecb5f31af54a4dac3b88de905115e7
Source dataset
uspto-grants-2000_05
Patent number
US06060487

Reaction notes

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