Sodium borohydride → 4-Methyl-4-(4-pyridin-3-yl-imidazol-1-yl)-pentan-1-ol

HRID 2055132Notes

Reaction equation

HRID 2055132 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]([CH3:19])([N:8]1[CH:12]=[C:11]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[N:10]=[CH:9]1)[CH3:7].[BH4-].[Na+]>C(O)C>[CH3:19][C:6]([N:8]1[CH:12]=[C:11]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[N:10]=[CH:9]1)([CH3:7])[CH2:5][CH2:4][CH2:3][OH:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 207376634-Methyl-4-(4-pyridin-3-yl-imidazol-1-yl)pentanoic acid methyl ester

Product 1

HCID 235114074-Methyl-4-(4-pyridin-3-yl-imidazol-1-yl)-pentan-1-olYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-methyl-4-(4-pyridin-3-yl-imidazol-1-yl)pentanoic acid methyl ester (1 eq) in ethanol was added sodium borohydride (4 eq) at room temperature. The reaction mixture was heated in a 50° C. oil bath for 60 minutes and then quenched by addition of H2O. Once the reaction solvent was removed in vacuo, a solution of the residue in dichloromethane was washed with NaCl (sat.), dried over sodium sulfate, filtered and concentrated to give 4-methyl-4-(4-pyridin-3-yl-imidazol-1-yl)-pentan-1-ol (68%). MH+(246)

Workup

  1. customquenched by addition of H2O
  2. customOnce the reaction solvent was removed in vacuo
  3. washa solution of the residue in dichloromethane was washed with NaCl (sat.)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-82d66e74acdc430aa9de4bb29e8499f7
Source dataset
uspto-grants-2008_02
Patent number
US07332476B2

Reaction notes

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