tert-Butyl 4-oxopiperidine-1-carboxylate → HCID 68743595, compound

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Reaction Steps

(2S)-2-Methyl-1-[6-(trifluoromethyl)-2,3-dihydro-1H -inden-1-yl]piperazine dihydrochloride (0.38 g, 1.3 mmol) was dissolved in dichloromethane. The solution was washed with saturated NaHCO3 solution, dried over MgSO4 and concentrated. The residue was taken up in dichloromethane (20 mL). To it were added tert-butyl 4-oxo-1-piperidinecarboxylate (0.32 g, 1.6 mmol) and titanium tetraisopropoxide (0.8 g, 3 mmol). The mixture was stirred at room temperature overnight and concentrated in vacuo. The residue was taken up in THF (20 mL). Diethylaluminum cyanide (0.18 g, 1.6 mmol) was added. After being stirred at room temperature for 5 hrs, the solution was quenched by addition of water (3 mL). The resulting solution was filtered through Celite and the Celite was washed with dichloromethane several times. The filtrate was dried over MgSO4 and concentrated to give the title compound (0.72 g, 98%) as a brown viscous oil. MS calculated for C26H35F3N4O2: (M+H)+493; found 493.2.

Provenance & Evidence