Water → HCID 89284731, compound

HRID 714887Notes

Reaction equation

HRID 714887 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]([N:15]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[N:17]=[CH:16]1)([CH3:14])[C:9](OCC)=[O:10].O.[OH-].[Na+]>O1CCCC1>[CH3:14][C:8]([N:15]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[N:17]=[CH:16]1)([CH3:7])[CH2:9][OH:10]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 117840630HCID 117840630, compound

Product 1

HCID 89284731HCID 89284731, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of lithium aluminium hydride (400 mg) in tetrahydrofuran (50 mL) was added a solution of ethyl 2-methyl-2-(4-nitro-1H-imidazol-1-yl)propanoate (2.0 g) obtained in Step A of Example 306 in tetrahydrofuran (20 mL) in an ice bath, and the mixture was stirred at room temperature for 1 hr. To the reaction mixture were added water and 2M aqueous sodium hydroxide solution, the insoluble substance was removed by filtration through Celite, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol) to give the title compound (260 mg).

Workup

  1. customthe insoluble substance was removed by filtration through Celite
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-ed510d479eb940dfa24140ef98b93776
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

Loading…