Imidazole → HCID 20714291, compound

HRID 2270091Notes

Reaction equation

HRID 2270091 reaction equation
[CH2:1]([C:3]1[C:12]([CH3:13])=[CH:11][C:10]2[C:5](=[C:6]([C@@H:14]([OH:17])[CH2:15][OH:16])[CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH3:2].ClCCl.N1C=CN=C1.[C:26]([Si:30]([CH3:33])([CH3:32])Cl)([CH3:29])([CH3:28])[CH3:27]>O>[CH2:1]([C:3]1[C:12]([CH3:13])=[CH:11][C:10]2[C:5](=[C:6]([C@H:14]([OH:17])[CH2:15][O:16][Si:30]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:33])[CH3:32])[CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6344DichloromethaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 20714287HCID 20714287, compound

Product 1

HCID 20714291HCID 20714291, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

1.72 g (7.45 mmol) of (−)-2-ethyl-3-methyl-8-(1(R),2-dihydroxyethyl)quinoline, 25 ml of dichloromethane and 0.75 g of imidazole are introduced into a 100 ml round-bottomed flask. The mixture is cooled to 0° C., 1.12 g (7.45 mmol) of tert-butyldimethylchlorosilane are added and the resulting mixture is stirred for 2 hours at 0° C. 50 ml of water are added and this mixture is extracted with ethyl acetate (3×80 ml). The organic phases are combined, dried over magnesium sulphate and concentrated. The residue is purified by chromatography on a column of silica (elution solvent: 10% ethyl acetate in hexane). 1.85 g (yield: 72%) of (+)-2-ethyl-3-methyl-8-(1(S)-hydroxy-2-[tert-butyldimethylsilyloxy]-ethyl)quinoline are obtained in the form of an oil.

Workup

  1. extractionthis mixture is extracted with ethyl acetate (3×80 ml)
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated
  4. customThe residue is purified by chromatography on a column of silica (elution solvent: 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-9864dbc137084550b0aa9cdf3c2e9387
Source dataset
uspto-grants-2001_12
Patent number
US06331549B1

Reaction notes

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