Water → HCID 58896161, compound

Participants

Reaction Steps

A mixture of 2-chloro-4′-cyano-3′,4′,5′,6′-tetrahydro-2′H-[3,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (6 g) and lithium tri-tert-butoxyaluminohydride (72.34 ml), 1M solution in THF) in 1-4-dioxane (90 ml) was refluxed overnight. After cooling, 1 N NaOH (100 ml) and H2O (100 ml) were added slowly at 0° C. Dichloromethane was added to the mixture. The aqueous phase was extracted twice with dichloromethane and the combined organic layers were washed with saturated sodium bicarbonate, dried (magnesium sulfate), filtered and concentrated in vacuo. The crude product was purified by chromatography [SiO2; dichloromethane-methanol (95:5)] to give 5.5 g (46%) of 7-Aza- spiro[indoline-3,4′-piperidine]-1′-carboxylic acid tert-butylester; MS (ES+) 290 (M+H+).

Provenance & Evidence