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Then, to a solution of 2.8 ml of oxalyl chloride in 100 ml of dichloromethane were added dropwise 4.6 ml of dimethyl sulfoxide in a dry ice-acetone bath while stirring, a solution of 5.9 g of the 2-bromo-6-(3-hydroxypyrrolidin-1-yl)pyridine in 50 ml of dichloromethane and finally 17 ml of triethylamine, and the temperature was returned to room temperature over 1 hour. The reaction mixture was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated. To the residue were added 50 ml of toluene, 7 ml of ethylene glycol and a catalytic amount of p-toluenesulfonic acid monohydrate, followed by heating under reflux for 3 hours while removing water. After cooling, it was washed with a saturated aqueous sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography with 5–7% ethyl acetate/hexane, to give 6.3 g of the title compound.

1. washThe reaction mixture was washed with water and brine
2. dry with materialdried over anhydrous magnesium sulfate
3. concentrationconcentrated
4. additionTo the residue were added 50 ml of toluene, 7 ml of ethylene glycol
5. temperatureby heating
6. temperatureunder reflux for 3 hours
7. customwhile removing water
8. temperatureAfter cooling
9. washit was washed with a saturated aqueous sodium hydrogen carbonate solution and brine
10. dry with materialdried over anhydrous magnesium sulfate
11. concentrationconcentrated