Trimethylsilyldiazomethane → HCID 178430275, compound

Participants

Reaction Steps

To a solution of (trimethylsilyl)diazomethane (2.0 M in hexane, 9.86 mL, 19.7 mmol) in tetrahydrofuran (40 mL) at 0° C. under an atmosphere of nitrogen was added n-butyllithium (2.5 M in hexane, 7.9 mL, 19.7 mmol) dropwise. After 30 min, a solution of 1-benzyl-4-(3-cyanophenyl)-3,4-dimethylpiperidine (Preparation 3, 5.0 g, 16.4 mmol) in tetrahydrofuran (40 mL) was added such that the internal temperature remained at 0° C. After stirring overnight, the reaction was quenched with saturated aqueous sodium hydrogencarbonate (100 mL) and the mixture was extracted with ethyl acetate (3×100 mL). The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give a pale brown foam (6.53 g, 79%).

Provenance & Evidence