Water → (+)-2-phenyl-3-methyl-8-(1-(R)-[2-(R)-methylpiperidino]-2-hydroxyethyl)quinoline

Participants

Reaction Conditions

Reaction Steps

A solution of 0.5 g (1.05 mmol) of 2-phenyl-3-methyl-8-(1-(R)-[2-(R)-methylpiperidino]-2-[tert-butyldimethylsilyloxy]ethyl)quinoline in a mixture of 15 ml of acetic acid, 5 ml of tetrahydrofuran and 5 ml of distilled water is heated at 70° C. for 40 hours and is then poured onto an ice-cold mixture of 150 ml of ethyl ether and of 150 ml of a saturated sodium hydrogencarbonate solution. The addition of sodium hydrogencarbonate is continued until a pH of approximately 9 is obtained. The mixture is then extracted with 3×200 ml of ethyl ether. The organic phases are combined, dried over magnesium sulfate, filtered and evaporated under vacuum. The residue is purified by silica gel chromatography (eluent: dichloromethane/methanol 9/1) to provide 0.3 g of (+)-2-phenyl-3-methyl-8-(1-(R)-[2-(R)-methylpiperidino]-2-hydroxyethyl)quinoline in the form of a colorless wax. (Yield: 75%)

Provenance & Evidence