Methyl iodide → Benzyl 3-methyl-2-oxo-1-{[2-(trimethylsilyl)ethoxy]methyl}-2,2',3,3'-tetrahydro-1H,1'H-spiro[1,8-naphthyridine-4,4'-pyridine]-1'-carboxylate

Participants

Reaction Steps

Lithium hexamethyldisilylazide (1.0 M in THF; 0.135 mL, 0.135 mmol) was added to solution of benzyl 2-oxo-1-{[2-(trimethylsilyl)ethoxy]methyl}-2,2′,3,3′-tetrahydro-1H,1′H-spiro[1,8-naphthyridine-4,4′-pyridine]-1′-carboxylate (50.0 mg, 0.104 mmol) in tetrahydrofuran (1 mL) at −78° C. After 40 min, iodomethane (8.0 μL, 0.135 mmol) was added and the reaction mixture was slowly warmed to ambient temperature. After 1 h, the mixture was quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate (3×). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated to give the title compound. MS 494.3 (M+1).

Provenance & Evidence