Acetone → 1-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-(1-hydroxyethyl)imidazole-5-carbonitrile

HRID 52920Notes

Reaction equation

HRID 52920 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[N:7]=[C:8]([CH2:33][CH2:34][CH2:35][CH3:36])[N:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:16][CH:15]=2)[C:10]=1[C:11]#[N:12])(=[O:5])[CH3:4].CC(C)=O>C(O)C>[C:29]([O:28][C:26]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:9]2[C:10]([C:11]#[N:12])=[C:6]([CH:3]([OH:5])[CH3:4])[N:7]=[C:8]2[CH2:33][CH2:34][CH2:35][CH3:36])=[CH:15][CH:16]=1)=[O:27])([CH3:32])([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydride2×HCID 190361124-Acetyl-1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-5-cyanoimidazole

Product 1

HCID 190362351-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-(1-hydroxyethyl)imidazole-5-carbonitrileYield 99.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.098 g of sodium borohydride was added to a solution of 1.18 g of 4-acetyl-1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butylimidazole-5-carbonitrile [prepared as described in step (a) above] in 30 ml of ethanol, and the resulting mixture was stirred at room temperature for 1 hour. The excess sodium borohydride was decomposed by adding acetone, and then the reaction mixture was concentrated by evaporation under reduced pressure. The residue was diluted with an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was dried and concentrated by evaporation under reduced pressure. The oily residue was purified by column chromatography through silica gel, using a 3:2 by volume mixture of ethyl acetate and hexane as the eluent, to afford 1.18 g of the title compound as a viscous oil.

Workup

  1. concentrationthe reaction mixture was concentrated by evaporation under reduced pressure
  2. additionThe residue was diluted with an aqueous solution of sodium chloride
  3. extractionextracted with ethyl acetate
  4. customThe extract was dried
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe oily residue was purified by column chromatography through silica gel
  7. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-03392fbbd4a347f9bfe4f71b3badbc66
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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