Trimethylsilyldiazomethane → HCID 178444685, compound

Participants

Reaction Steps

To a solution of (trimethylsilyl)diazomethane (2.0 M in hexane, 400 μL, 0.80 mmol) in tetrahydrofuran (10 mL) at 0° C. under an atmosphere of nitrogen was added n-butyllithium (2.5 M in diethyl ether, 320 μL, 0.80 mmol) dropwise. After 20 min, a solution of 4-(3-cyanophenyl)-1-hexyl-3,4-dimethylpiperidine (Preparation 6, 200 mg, 0.67 mmol) in tetrahydrofuran (5 mL) was added such that the internal temperature remained at 0° C. After stirring overnight, the reaction was quenched with saturated aqueous sodium hydrogencarbonate (25 mL) and the mixture was extracted with diethyl ether (3×25 mL). The extracts were washed with water and brine (10 mL each), dried over MgSO4, filtered and concentrated in vacuo to give the title compound as a white foam which was used without further purification (266 mg, 96%).

Provenance & Evidence