tert-Butyl 4-oxopiperidine-1-carboxylate → HCID 67264921, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve {2-[4-(3-chloro-4-fluoro-phenyl)-imidazol-1-yl]-ethyl}-dimethylamine (1.00 equiv; 4.07 mmol; 1.09 g) in anhydrous THF (15 mL; 184.33 mmol) and cool the mixture to −78° C. Slowly add n-butyl lithium (1.40 equiv; 5.70 mmol; 3.56 mL) (1.6M Aldrich), and stir at −78° C. for 30 min, then add a THF (10 mL) solution of N-t-butoxycarbonyl-4-piperidone (1.20 equiv; 4.89 mmol; 973.43 mg) dropwise over 10 min. After 20 min, warm the reaction to RT and stir 3 h. Partition between EA and water. Wash the organic layer with brine, NaCl aq (50/50) and dry over MgSO4. Filter and concentrate. Purify the residue by ISCO chromatography over a Biotage 40M column eluting with 100% DCM to 10% MeOH/DCM to give 785 mg (41%) of the title compound as a white solid. ES(MS): (m/z)=467.0 (M+H).

Provenance & Evidence