Water → (+)-2-ethyl-3-methyl-8-(1(R)-diethylamino-2-hydroxyethyl)quinoline

HRID 2270093Notes

Reaction equation

[CH2:1]([C:3]1[C:12]([CH3:13])=[CH:11][C:10]2[C:5](=[C:6]([CH:14]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[CH2:15][O:16][Si](C(C)(C)C)(C)C)[CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH3:2].O.O.O.[F-].C([NH3+])(C)(C)C.O>O1CCCC1>[CH2:1]([C:3]1[C:12]([CH3:13])=[CH:11][C:10]2[C:5](=[C:6]([C@@H:14]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[CH2:15][OH:16])[CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

0.40 g (1.0 mmol) of (+)-2-ethyl-3-methyl-8-(1-diethylamino-2-[tert-butyldimethylsilyloxy]ethyl)-quinoline and 5 ml of tetrahydrofuran are introduced into a 50 ml round-bottomed flask. This solution is cooled to 0° C. on an ice bath and a solution of 0.40 g (1.52 mmol) of tert-butylammonium fluoride trihydrate in 10 ml of tetrahydrofuran is added. The reaction mixture is stirred at 45° C. for 3 hours. 50 ml of water are added and the resulting mixture is extracted with ethyl acetate (3×50 ml). The organic phases are combined, dried over magnesium sulphate and concentrated under vacuum. The residue is purified by chromatography on a column of silica (elution solvent: 5% methanol in dichloromethane). 0.25 g (yield: 87.4%) of (+)-2-ethyl-3-methyl-8-(1(R)-diethylamino-2-hydroxyethyl)quinoline is obtained in the form of an oil.

Workup

extractionthe resulting mixture is extracted with ethyl acetate (3×50 ml)
dry with materialdried over magnesium sulphate
concentrationconcentrated under vacuum
customThe residue is purified by chromatography on a column of silica (elution solvent: 5% methanol in dichloromethane)

Sources & evidence

ORD record: ord-66bea9d472e541af92fcae4c9aa263f6
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06331549B1

Reaction notes

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