Water → HCID 58692401, compound

Participants

Reaction Conditions

Reaction Steps

Water (50 mL) and potassium hydroxide (11.9 g, 213 mmol) were added to a solution of tert-butyl 4-(cyanomethyl)-4-(3,4-dimethylphenyl)piperidine-1-carboxylate 8-4 (14.0 g, 42.6 mmol) in ethanol (200 mL). The reaction was heated at approximately 90° C. until complete conversion of starting material (as monitored by high-pressure liquid chromatography). The reaction mixture was then cooled to ambient temperature, quenched with ice cold 1 N aqueous hydrochloric acid (500 mL) and extracted with ethyl acetate (3×500 mL). The organic phase was washed with brine, dried (magnesium sulfate) and concentrated in vacuo to give a crude residue. Purification of the crude residue by flash chromatography over silica gel (gradient elution; 20%-40% ethyl acetate/hexanes as eluent) afforded compound 8-5 as a white solid.

Provenance & Evidence