Isoamyl Nitrite → HCID 86676259, compound

Participants

Reaction Steps

Add potassium 2-methylpropan-2-olate (66.1 g, 588.8 mmol) to a solution of 5-[2-(tert-butyl(dimethyl)silyl)oxyethyl]-7H-pyrido[2,3-d][3]benzazepin-6-one (155.0 g, 420.6 mmol) in tetrahydrofuran (1.6 L) at −5° C. and stir for 10 minutes. Add isoamyl nitrite (61.9 mL, 462.6 mmol) dropwise at −5° C. and stir mixture for 10 minutes. Pour over ice/water (2 L) and extract with ethyl acetate (3×200 mL). Wash combined organics with brine (200 mL), dry over sodium sulfate. Add toluene (1 L) and concentrate (×3) to obtain the title compound as a thick brown oil (160.0 g, 402.5 mmol, 96%). MS (m/z): 398 (M+1).

Provenance & Evidence