Imidazole → HCID 59556914, compound

HRID 1967309Notes

Reaction equation

HRID 1967309 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C@@H:9]([CH3:12])[CH2:10][OH:11])[CH:5]=[CH:6][CH:7]=1.N1C=CN=C1.[C:18]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])([CH3:20])[CH3:19].O>CN(C)C=O>[Si:22]([O:11][CH2:10][C@@H:9]([NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH3:12])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 59556957HCID 59556957, compound

Product 1

HCID 59556914HCID 59556914, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (2S)-2-[(3-chlorophenyl)amino]propane-1-ol (7.00 g) in N,N-dimethylformamide (19 mL) were added imidazole (2.82 g) and tert-butyl(chloro)dimethylsilane (6.38 g), and the mixture was stirred at 50° C. for 14 hr. Water (200 mL) was added to the reaction solution, and the mixture was extracted with diethyl ether. The obtained organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=0→40%) to give the title compound as a colorless oil (yield: 7.40 g, 65%).

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=0→40%)

Sources & evidence

ORD record
ord-178d00a00fab440c80846e7db904c3d2
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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