Potassium Sodium Tartrate → HCID 11586806, compound

Participants

Reaction Steps

N-acetyl-2-(3-acetyl-2-ethylindolizin-1-yl)acetamide (330 mg, 1.3 mmol) isolated in Example 5 was stirred in anhydrous ethyl ether (120 mL) to which lithium aluminum hydride (330 mg) was added. The reaction mixture was heated in a nitrogen atmosphere under reflux overnight. After cooling to room temperature, Rochelle salt was added with stirring until everything dissolved. The phases were separated and the aqueous phase was extracted with ether one time. Evaporation of the organic phase gave a residue, which was purified by flash column chromatography on silica gel eluting with 3-10% methanol in methylene chloride containing 1% ammonium hydroxide. The product (110 mg) was dissolved in ethanol, treated with a solution of fumaric acid (110 mg) dissolved in ethanol and evaporated to give a residue which was recrystallized from methyl ethyl ketone. The title compound was obtained as a greenish-tan solid, mp: 154-158° C. Mass spectrum: [M+H]+ 245 m/z.

Provenance & Evidence