4-Nitrobenzenethiol → Tert-butyl 4-[(4-nitrophenyl)sulfanyl]piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

4-Nitrobenzenethiol (5.93 mmol, 1.15 g), and sodium hydride (8.12 mmol, 0.325 g) were combined in tetrahydrofuran and stirred at 0° C. for 30 minutes. tert-Butyl 4-(methyl-sulfonyloxy)piperidine-1-carboxylate (8.89 mmol, 2.484 g) was added and the reaction mixture heated at 60° C. overnight. The reaction mixture was concentrated under vacuum and residue dissolved in dichloromethane and washed with water. The organic layer was separated, dried and concentrated under vacuum. The residue was purified by silica column chromatography (eluent: dichloromethane) to afford the title compound (1.45 g). MS (ESI) m/z 339.5 [M+H]+

Provenance & Evidence