Dimethyl Sulfoxide → HCID 22884890, compound

Participants

Reaction Steps

A 1-l 3-necked, round-bottomed flask equipped with a magnetic stirrer was charged with 2.0 g (6.44 mol) of 6-hydroxycinchonine (1) and 10 ml of DMSO which had been dried over molecular sieves. To the stirred solution was added very slowly over a period of 0.5 h 2.8 ml (7.0 mmol) of n-butyl lithium (2.5M/hexane, Aldrich). The reaction flask was cooled with an ice-water bath and then treated with 1.6 ml (13.57 mmol) of ethyl iodoacetate. The temperature was allowed to rise to room temperature over a period of 2 h and the mixture was stirred at room temperature for 1 h. The reaction mixture was poured into 65 ml of deionized water and 15 ml of ethyl acetate during which some of the product oiled out. 100 ml of dichloromethane was added to dissolve the oily product and produce two layers. The heterogeneous brown mixture was concentrated under reduced pressure to remove the organic solvents during which the product precipitated. The mixture was left to stand overnight in the refrigerator. The precipitate was collected and washed with ETOAc and yielded 1.6 g (41%) of (S)-8-ethenyl-2-[hydroxy-6-(2-ethoxy-2-oxoethoxy)-4-quinolinylmethyl]-1-(2-ethoxy-2-oxoethyl)azoniabicyclo[2.2.2]octane iodide as an off-white solid. NMR, IR and MS data confirmed compound identity.

Provenance & Evidence