Trimethylsilyldiazomethane → HCID 178421608, compound

Participants

Reaction Steps

To a solution of (trimethylsilyl)diazomethane (2.0 M in hexane, 0.55 mL, 1.10 mmol) in tetrahydrofuran (5 mL) at 0° C. under an atmosphere of nitrogen was added n-butyllithium (1.6 M in hexane, 0.69 mL, 1.10 mmol) dropwise. After 1 h, a solution of 1-benzyl-4-(3-cyanophenyl)-4-methylpiperidine (Preparation 9, 300 mg, 1.03 mmol) in tetrahydrofuran (10 mL) was added such that the internal temperature remained at 0° C. After 4.5 h, the reaction was quenched with saturated sodium hydrogencarbonate (25 mL) and the mixture was extracted with diethyl ether (3×25 mL). The extracts were washed with water (10 mL) and brine (10 mL), dried over Na2SO4, filtered and concentrated in vacuo to give the title compound as a foam (360 mg, 86%).

Provenance & Evidence