Sodium borohydride → HCID 178442100, compound

HRID 230824Notes

Reaction equation

HRID 230824 reaction equation
[CH2:1]([C:3]([C:17]1[CH:30]=[CH:29][C:20]([O:21][CH2:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[C:19]([CH3:31])[CH:18]=1)([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[NH:16][N:15]=[N:14][N:13]=2)=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2].[BH4-].[Na+]>CCO>[CH2:1]([C:3]([C:17]1[CH:30]=[CH:29][C:20]([O:21][CH2:22][CH:23]([OH:28])[C:24]([CH3:25])([CH3:27])[CH3:26])=[C:19]([CH3:31])[CH:18]=1)([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[NH:16][N:15]=[N:14][N:13]=2)=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178442099HCID 178442099, compound

Product 1

HCID 178442100HCID 178442100, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 1-(4-{1-Ethyl-1-[4-(1H-tetrazol-5-yl)-phenyl]-propyl}-2-methyl-phenoxy)-3,3-dimethyl-butan-2-one (0.37 g, 0.88 mmol) and EtOH (5 mL) was added NaBH4 (0.037 g, 0.97 mmol) and the solution stirred for 1 hour. The solids were removed by filtration and the solution concentrated. The residue was purified by ISCO (10-30 [89% EtOAc:10% MeOH:1% AcOH] gradient) to furnish the title compound (0.32 g, 0.76 mmol, 86%).

Workup

  1. customThe solids were removed by filtration
  2. concentrationthe solution concentrated
  3. customThe residue was purified by ISCO (10-30 [89% EtOAc:10% MeOH:1% AcOH] gradient)

Sources & evidence

ORD record
ord-5e73c3e3c25a42b8b0abd7f439b8cb50
Source dataset
uspto-grants-2009_07
Patent number
US07566803B2

Reaction notes

Loading…