Imidazole → HCID 58188321, compound

HRID 1845131Notes

Reaction equation

HRID 1845131 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C@@H:8]([OH:11])[CH2:9][OH:10])=[CH:4][CH:3]=1.N1C=CN=C1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>C(Cl)Cl>[Si:17]([O:10][CH2:9][C@@H:8]([C:5]1[CH:6]=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=1)[OH:11])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 58188367HCID 58188367, compound

Product 1

HCID 58188321HCID 58188321, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of (R)-1-(6-methylpyridin-3-yl)ethane-1,2-diol (13.72 g, 0.085 mol), 1H-imidazole (13.55 g, 0.197 mol), and CH2Cl2 (180 mL) at 0° C. was added tert-butyldimethylsilyl chloride (15.31 g, 0.098 mol). The reaction mixture was stirred at 0° C. for 30 minutes, then warmed to room temperature and stirred overnight. The mixture was washed with water (300 mL) and extracted with CH2Cl2. The combined organic layers were dried over sodium sulfate, and concentrated. The residue was purified by flash chromatography (0-50% EtOAc/hexane) to afford a colorless oil.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred overnight
  3. washThe mixture was washed with water (300 mL)
  4. extractionextracted with CH2Cl2
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (0-50% EtOAc/hexane)
  8. customto afford a colorless oil

Sources & evidence

ORD record
ord-73a44317f801484894252cff6aa665b8
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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