反应详情

35 ml (252 mmol) of triethylamine and 11.3 ml (101 mmol) of 4-chlorobutyryl chloride were successively added dropwise to a solution of 21.6 g (101 mmol) of 2-amino-1-phenyl-2-pyridin-2-ylethanol in 50 ml of DMF at 50° C. After 1 h at room temperature, 48.4 g of sodium hydroxide were added, and the mixture was stirred at room temperature for 1 h. The reaction mixture was poured into ice-water and extracted with methylene chloride, and the organic phases were washed with water and sodium bicarbonate solution. Chromatography on silica gel with ethyl acetate/ethanol 20:1 resulted in isolation of 3.0 g each of the syn- and anti-diastereomer of 1-(2-hydroxy-2-phenyl-1-pyridin-2-ylethyl)pyrrolidin-2-one in pure form. The relative stereochemistry was assigned by X-ray spectroscopy.

1. extractionextracted with methylene chloride
2. washthe organic phases were washed with water and sodium bicarbonate solution