Imidazole → HCID 18516372, compound

HRID 1369924Notes

Reaction equation

HRID 1369924 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CN=C1.[OH:14][CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]2[CH:21]3[CH2:30][CH2:29][CH2:28][CH:22]3[C:23](=[O:27])[NH:24][C:25]=2[CH:26]=1>CN(C=O)C.CCOCC>[Si:1]([O:14][CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]2[CH:21]3[CH2:30][CH2:29][CH2:28][CH:22]3[C:23](=[O:27])[NH:24][C:25]=2[CH:26]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 18516364HCID 18516364, compound

Product 1

HCID 18516372HCID 18516372, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

At 0° C., 0.62 g (5.4 mmol) of tert-butyldimethylsilyl chloride and 0.72 g (10.7 mol) of imidazole are added to a solution of 0.62 g (2.7 mmol) of 7-(2-hydroxyethyl)-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one in 10 ml of DMF. After 4 hours at room temperature, the batch is diluted with ether, washed with water, 10% citric acid and saturated NaHCO3, dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography with hexane-ethyl acetate on silica gel yields 0.79 g of product.

Workup

  1. washwashed with water, 10% citric acid and saturated NaHCO3
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-328d7d3222c14c83a45eb7c92669d8cf
Source dataset
uspto-grants-2003_06
Patent number
US06579883B1

Reaction notes

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