Water → 1,1-Dimethylethyl 4-[(6-chloro-8-quinolinyl)oxy]-1-piperidinecarboxylate

Participants

Reaction Conditions

Reaction Steps

6-Chloro-8-fluoroquinoline (for example, as prepared for Intermediate 5) (2.18 g, 12 mmol) was dissolved in NMP (20 ml) and treated with 1,1-dimethylethyl 4-hydroxy-1-piperidinecarboxylate (commercially available, for example, from Acros and/or Aldrich) (4.85 g, 24 mmol) and sodium tert-butoxide (2.38 g, 25 mmol). Further NMP was added (5 ml) and the resulting mixture was stirred at 140° C. for 1 h, and then allowed to cool overnight. The reaction mixture was treated with water and extracted with toluene. The organic extract was washed with water (×3), dried (MgSO4), and concentrated in vacuo. The residue was purified by silica chromatography (2×70 g), eluting with 0-100% EtOAc-cyclohexane over 30 min. The relevant fractions were concentrated in vacuo to give the title compound as a yellow gum (2.73 g, 63%): LCMS RT=3.37 min, ES+ve m/z 363/365 [M+H]+.

Provenance & Evidence