Methanol → 1-(tert-Butoxycarbonyl)-4-(pyridin-3-yl)piperidine-4-carboxylic acid

Participants

Reaction Steps

A flask was charged with tert-butyl 4-cyano-4-(pyridin-3-yl)piperidine-1-carboxylate (7.5 g, 26.1 mmol) and NaOH (50% in water, 100 mL) in ethanol (100 ml) and heated at reflux for 6 h. The ethanol was removed, and the resulting solution was acidified to pH=5 using concentrated hydrochloric acid. The desired product was collected by filtration, and dried overnight to yield 4.1 g (51%). Mass Spec.: 307.18 (MH)+. LC tr=1.31 min (Phenomenex-Luna 4.6×50 mm S10, 10% MeOH/90% H2O/0.1% TFA→90% MeOH/10% H2O/0.1% TFA Gradient Time=2 min, Flow rate=4 mL/min)

Provenance & Evidence