Methyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-formylimidazole-5-carboxylate → Methyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-(1-hydroxy-2,2-dimethylpropyl)imidazole-5-carboxylate

HRID 265086Notes

Reaction equation

HRID 265086 reaction equation
[C:1]([Mg]Br)([CH3:4])([CH3:3])[CH3:2].[C:7]([O:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[CH:25]=[CH:24][C:23]([CH2:26][N:27]2[C:31]([C:32]([O:34][CH3:35])=[O:33])=[C:30]([CH:36]=[O:37])[N:29]=[C:28]2[CH2:38][CH2:39][CH2:40][CH3:41])=[CH:22][CH:21]=1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>O1CCCC1.C(OCC)(=O)C.[Cl-].[NH4+]>[C:7]([O:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[CH:25]=[CH:24][C:23]([CH2:26][N:27]2[C:31]([C:32]([O:34][CH3:35])=[O:33])=[C:30]([CH:36]([OH:37])[C:1]([CH3:4])([CH3:3])[CH3:2])[N:29]=[C:28]2[CH2:38][CH2:39][CH2:40][CH3:41])=[CH:22][CH:21]=1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 2

HCID 19036345Methyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-formylimidazole-5-carboxylateHCID 178418586HCID 178418586, compound

Product 1

HCID 19036062Methyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-(1-hydroxy-2,2-dimethylpropyl)imidazole-5-carboxylate

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

2.77 ml of a 2M solution of t-butylmagnesium bromide in tetrabydrofuran were added at -55° C. and under an atmosphere of nitrogen to a solution of 1.32 g of methyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-formylimidazole-5-carboxylate [prepared as described in step (a))above] in 26 ml of tetrahydrofuran, and the resulting mixture was stirred at a temperature of -55° C. to -50° C. for 30 minutes. At the end of this time, the reaction mixture was diluted with 50 ml of ethyl acetate and with a saturated aqueous solution of ammonium chloride. The organic layer was separated and dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel, using a 2:1 by volume mixture of hexane and ethyl acetate as the eluent, to afford 0.87 g of the title compound as an amorphous solid.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was removed by distillation under reduced pressure
  4. customThe residue was purified by column chromatography through silica gel
  5. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-8bfa6eb0eb984383b052d4f706c392ef
Source dataset
uspto-grants-1997_07
Patent number
US05646171

Reaction notes

Loading…