Hexane → HCID 18922011, compound

Participants

Reaction Conditions

Reaction Steps

62 mg of N-[1-(4-oxopentyl)piperidin-4-yl]-2-cyclobutyl-2-hydroxy-2-phenylacetamide was added at 0° C. to an ylide compound prepared from 124 mg of ethyltriphenylphosphonium bromide and 200 μl of n-butyl lithium (as a 1.62M hexane solution), and this mixture was stirred at 0° C. for 30 minutes and then at room temperature for 4 hours. After the solvent was distilled off under reduced pressure, the resulting residue was mixed with 20 ml of water and then extracted with chloroform (30 ml×3). The organic layer was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by preparative thin-layer chromatography [Kieselgel™ 60F254, Art 5744 (manufactured by E. Merck); developing solvent: chloroform to chloroform/methanol=10/1) to obtain 18.0 mg of N-[1-(Z)-(4-methyl-4-hexenyl)piperidin-4-yl]-2-cyclobutyl-2-hydroxy-2-phenylacetamide and 9.0 mg of N-[1-(E)-(4-methyl-4-hexenyl)piperidin-4-yl]-2-cyclobutyl-2-hydroxy-2-phenylacetamide.

Provenance & Evidence