Ammonium Acetate → 1-[8-(4-{[tert-Butyl(dimethyl)silyl]oxy}piperidin-1-yl)-5-chloroquinolin-7-yl]ethanamine

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-[8-(4-{[tert-butyl(dimethyl)silyl]oxy}piperidin-1-yl)-5-chloroquinolin-7-yl]ethanone (275 mg, 0.656 mmol) and ammonium acetate (506 mg, 6.56 mmol) in methanol (3.7 mL) and acetonitrile (3.7 mL) was heated at 65° C. in a sealed tube for 30 minutes. After cooling to room temperature, sodium cyanoborohydride (82.5 mg, 1.31 mmol) was added to the resulting mixture. The reaction was heated at 65° C. for another 4 hours, then cooled to room temperature, quenched with sat. sodium bicarbonate and extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and evaporated to dryness. The residue was used directly in the next step. LCMS calculated for C22H35ClN3OSi (M+H)+: m/z=421.2; Found: 421.1.

Provenance & Evidence