Sodium borohydride → 3-[3-(2-Bromobenzyl)-3H-imidazole-4-yl]propan-1-ol

HRID 76893Notes

Reaction equation

HRID 76893 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1[N:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Br:18])[CH:8]=[N:9][CH:10]=1.[BH4-].[Na+]>CO>[Br:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][N:7]1[C:6]([CH2:5][CH2:4][CH2:3][OH:2])=[CH:10][N:9]=[CH:8]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 588271303-[3-(2-Bromobenzyl)-3H-imidazol-4-yl]propionic acid methyl ester

Product 1

HCID 588271793-[3-(2-Bromobenzyl)-3H-imidazole-4-yl]propan-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-[3-(2-bromobenzyl)-3H-imidazol-4-yl]propionic acid methyl ester (1.89 g, 5.85 mmol) in MeOH at 0° C. is added NaBH4 and the resulting mixture is stirred at 0° C. for 1 h and warmed up to ambient temperature. The mixture is stirred at ambient temperature for 3 h and is quenched with saturated aqueous NH4Cl, and is adjusted pH to 7 with saturated aqueous Na2CO3. Then the reaction mixture is concentrated and extracted by CH2Cl2. The organic layer is washed with half saturated aqueous NaCl, dried over anhydrous Na2SO4, and concentrated to yield a white solid. MS (ESI) m/z 295 (M+H).

Workup

  1. temperaturewarmed up to ambient temperature
  2. stirringThe mixture is stirred at ambient temperature for 3 h
  3. customis quenched with saturated aqueous NH4Cl
  4. concentrationThen the reaction mixture is concentrated
  5. extractionextracted by CH2Cl2
  6. washThe organic layer is washed with half saturated aqueous NaCl
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. customto yield a white solid

Sources & evidence

ORD record
ord-bc7362e02f8e45c8840e560d3967dcc2
Source dataset
uspto-grants-2014_09
Patent number
US08835646B2

Reaction notes

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