ethyl quinoline-3-carboxylate → Ethyl 1,2,3,4-tetrahydroquinoline-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

Borane-pyridine complex (8 M, 292 mL, 2.34 mmol) was added to a solution of Ethyl quinoline-3-carboxylate (235 mg, 1.17 mmol) in acetic acid (10 mL). The solution was stirred at 25° C. for 20 h. The reaction mixture was concentrated in vacuo, basified with 1 M sodium carbonate (30 mL), and the product was extracted with dichloromethane (3×35 mL). The organic layers were dried over sodium sulfate and concentrated. Purification of the product by flash column chromatography (10% to 20% EtOAc/hexane) afforded the title compound (239 mg, 1.15 mmol). MS m/z: 206 (M+1).

Provenance & Evidence