Water → HCID 67243506, compound

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Reaction Steps

A mixture of 5-chloro-4′-cyano-3-fluoro-3′,4′,5′,6′-tetrahydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (0.05 g) and lithium tri-tert-butoxyaluminohydride (0.57 ml), 1M solution in THF) in 1-4-dioxane (0.75 ml) was refluxed under nitrogen for 4 hrs. After cooling, 1 N NaOH and H2O and ethyl acetate were added slowly to the mixture at 0° C. The aqueous phase was extracted twice with ethyl acetate and the combined organic layers were washed with saturated sodium bicarbonate, dried (sodium sulfate), filtered and concentrated in vacuo. The crude product was purified by chromatography [SiO2; hexane-ethyl acetate-triethylamine (75:25:1)] to give 18 mg g (38%) of 6-chloro-4-aza-spiro[indoline-3,4′-piperidine]-1′-carboxylic acid tert-butylester; MS (ES+) 324 (M+H+).

Provenance & Evidence