Imidazole → HCID 24824074, compound

HRID 1823073Notes

Reaction equation

HRID 1823073 reaction equation
[CH2:1]([N:8]([CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=1)[CH2:9][C@@H:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1)[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:33](Cl)([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34]>CN(C)C=O>[CH2:1]([N:8]([CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=1)[CH2:9][C@H:10]([O:11][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 24822638HCID 24822638, compound

Product 1

HCID 24824074HCID 24824074, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (1R)-2-[benzyl[2-(4-bromophenyl)ethyl]amino]-1-(3-chlorophenyl)ethanol (18.5 g) in N,N-dimethylformamide (40 ml) were successively added imidazole (3.96 g) and tert-butyldimethylsilyl chloride (7.52 g) and the solution was stirred at room temperature for 14 hours. The reaction mixture was quenched by the addition of water (100 ml) and extracted with ethyl acetate (100 ml×1). The extract was washed with water (100 ml×2), brine (100 ml×1), and dried over magnesium sulfate. Filtration followed by evaporation gave a colorless oil, which was chromatographed on silica gel (eluent:hexane/ethyl acetate) to give (2R)-N-benzyl-N-[2-(4-bromophenyl)ethyl]-2-[[tert-butyl(dimethyl)silyl]oxy]-2-(3-chlorophenyl)ethanamine (21.0 g) as a colorless oil.

Workup

  1. customThe reaction mixture was quenched by the addition of water (100 ml)
  2. extractionextracted with ethyl acetate (100 ml×1)
  3. washThe extract was washed with water (100 ml×2), brine (100 ml×1)
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration
  6. customfollowed by evaporation
  7. customgave a colorless oil, which
  8. customwas chromatographed on silica gel (eluent:hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d7c5a0b45d31462b99f17c35e5643826
Source dataset
uspto-grants-2006_05
Patent number
US07037938B2

Reaction notes

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