HCID 68431041, compound → HCID 68430555, compound

Participants

Reaction Steps

tert-Butyl 4-(1-propynyl)-1,2,3,6-tetrahydropyridine-1-carboxylate (410 mg) prepared in 3) of Example 7 was dissolved in 10% methanolic hydrochloric acid followed by stirring at room temperature for 3 hours and the solvent was evaporated in vacuo. The resulting residue was dissolved in 10 ml of methylene chloride and cooled down to 0° C. and 0.56 ml of triethylamine and 354 mg of isopropyl chloroformate were dropped thereinto. After raising its temperature to room temperature, the reaction was stopped by a saturated aqueous solution of sodium hydrogen carbonate. The product was extracted with ethyl acetate and the organic layer washed with a saturated aqueous solution of ammonium chloride and dried over sodium sulfate. After the solvent was evaporated, the residue was separate and purified by a silica gel column chromatography (hexane/ethyl acetate=4/1) to give 384 mg of a crude product of the title compound.

Provenance & Evidence