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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence