Ammonium Acetate → (3R)-1-[7-(1-aminoethyl)-5-chloroquinolin-8-yl]pyrrolidin-3-ol

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-{5-chloro-8-[(3R)-3-hydroxypyrrolidin-1-yl]quinolin-7-yl}ethanone (95 mg, 0.33 mmol) and ammonium acetate (252 mg, 3.27 mmol) in methanol (1.8 mL) and acetonitrile (1.9 mL) was heated at 65° C. in a sealed tube for 30 minutes. After cooling, sodium cyanoborohydride (41.1 mg, 0.653 mmol) was added to the resultant mixture. The reaction was heated at 65° C. for another 4 hours, then cooled to room temperature and quenched with saturated sodium bicarbonate. The mixture was then extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and evaporated to dryness (58 mg, 60%). The residue was used directly in the next step. LCMS calculated for C15H19ClN3O(M+H)+: m/z=292.1; found: 292.1.

Provenance & Evidence