Imidazole → HCID 18516391, compound

HRID 1369929Notes

Reaction equation

HRID 1369929 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][CH2:17][C:18]1[CH:19]=[CH:20][C:21]2[CH:22]3[CH2:31][CH2:30][CH2:29][CH:23]3[C:24](=[O:28])[NH:25][C:26]=2[CH:27]=1>CN(C=O)C.C(OCC)(=O)C>[Si:1]([O:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]2[CH:22]3[CH2:31][CH2:30][CH2:29][CH:23]3[C:24](=[O:28])[NH:25][C:26]=2[CH:27]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 18516382HCID 18516382, compound

Product 1

HCID 18516391HCID 18516391, compoundYield 105.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

At 0° C., 3.65 g (24.5 mmol) of tert-butyldimethylsilyl-chloride and 3.29 g (48.9 mol) of imidazole are added to a solution of 3.0 g (12.2 mmol) of 7-(3-hydroxypropyl)-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one in 50 ml of DMF. After 3 hours, the batch is diluted with ethyl acetate, 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 4.62 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-1404d5f3153941f685ca9c8c9301d263
Source dataset
uspto-grants-2003_06
Patent number
US06579883B1

Reaction notes

Loading…