2-(1-(2,3-Dimethylphenyl)ethyl)-1H-imidazole → 2-[(1R)-1-(2,3-Dimethylphenyl)ethyl]-1H-imidazole

HRID 734450Notes

Reaction equation

HRID 734450 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]([C:11]1[NH:12][CH:13]=[CH:14][N:15]=1)[CH3:10]>C(O)C>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:9]([C:11]1[NH:15][CH:14]=[CH:13][N:12]=1)[CH3:10]

Participants

3

Reactant 1

HCID 216625422-(1-(2,3-Dimethylphenyl)ethyl)-1H-imidazole

Product 1

HCID 247389342-[(1R)-1-(2,3-Dimethylphenyl)ethyl]-1H-imidazoleYield 49.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound of Example 1 (750 mg, 3.75 mmol) was dissolved in ethanol (4 ml) and the enantiomers were separated by automated preparative liquid chromatography (Gilson system, 50×50 mm ID Chiralcel OD, 20 μm column, 50 ml/min) using ethanol:hexane [10:90] as the mobile phase. The appropriate fractions were combined and concentrated to give the title compound (370 mg).

Workup

  1. customthe enantiomers were separated
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-5367994e5b5e42f29387eaf361af973d
Source dataset
uspto-grants-2009_09
Patent number
US07592362B2

Reaction notes

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