Pyridine → Ethyl 6-((1R,3S)-3-(4-(4-chlorophenyl)piperazin-1-yl)cyclopentane carboxamido)spiro[2.5]oct-5-ene-5-carboxylate

Participants

Reaction Steps

To an ice cold solution of ethyl 2-aminocyclohex-1-enecarboxylate (1.27 g, 6.48 mmol) in pyridine (5 ml), phosphorus trichloride (0.18 ml, 2.10 mmol) was added. After 15 min, (1R,3S)-3-(4-(4-chlorophenyl)piperazin-1-yl)cyclopentanecarboxylic acid (0.5 g, 1.62 mmol) was added at room temperature to the mixture, followed by stirring at temperature for 6 h. Upon completion, the reaction mixture was diluted with chloroform and the organic layer was washed with saturated aqueous sodium hydrogencarbonate solution, The organic layer was separated, dried over sodium sulphate and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography using ethyl acetate in hexane as eluent to afford ethyl 6-((1R,3S)-3-(4-(4-chlorophenyl)piperazin-1-yl)cyclopentanecarboxamido)spiro[2.5]oct-5-ene-5-carboxylate (300 mg, 38.1%).

Provenance & Evidence