Lithium Hydroxide → 6-((1S,3S)-3-(4-(4-chlorophenyl) piperazin-1-yl)cyclopentanecarboxamido)spiro[2.5]oct-5-ene-5-carboxylic acid

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Reaction Steps

Ethyl 6-((1R,3S)-3-(4-(4-chlorophenyl)piperazin-1-yl)cyclopentane carboxamido)spiro[2.5]oct-5-ene-5-carboxylate (0.3 g, 0.62 mmol) was dissolved in 10 ml of tetrahudrofuran/methanol/water (3:1:1). To this solution was added lithium hydroxide (0.12 g, 2.8 mmol). The mixture was stirred at room temperature overnight, concentrated, and acidified using 1 N hydrochloric acid to pH 6. To the resulting white slurry was added water (20 ml). The mixture was extracted with dichloromethane (2×50 ml). The organic layer was dried over sodium sulfate and concentrated to afford the title compound 6-((1R,3S)-3-(4-(4-chlorophenyl)piperazin-1-yl)cyclopentane carboxamido)spiro[2.5]oct-5-ene-5-carboxylic acid along with its corresponding diastereomer 6-((1S,3S)-3-(4-(4-chlorophenyl) piperazin-1-yl)cyclopentanecarboxamido)spiro[2.5]oct-5-ene-5-carboxylic acid as observed on the HPLC column.

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