Hydrochloric Acid → HCID 67442431, compound

Participants

Reaction Steps

To a suspension of 3-(6-(methoxycarbonyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinolin-2-yl)benzoic acid (150 mg, 0.44 mmol.) in dichloromethane (10 mL) was added N-hydroxybenzotriazole (89.2 mg, 0.66 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide.hydrochloric acid (253 mg, 1.32 mmol.), followed by 4-methylmorpholine (133.5 mg, 1.32 mmol) and the resultant mixture was stirred at room temperature for 1 h. Then tetrahydrofuran-3-amine (57.5 mg, 0.66 mmol) was added to the flask and the reaction mixture was stirred under nitrogen overnight. Thin layer chromatography (petroleum ether:ethyl acetate=1:1) and LC-MS showed the reaction was complete. The reaction was quenched with water and extracted with dichloromethane (twice). The combined organic layers were washed with 2% sodium hydroxide aqueous solution (twice) and water (3 times), dried over anhydrous sodium sulfate. Removal of the solvent in vacuo gave 236 mg methyl 3,3-dimethyl-2-(3-(tetrahydrofuran-3-ylcarbamoyl)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate of as a white solid, which was dissolved in methanol and treated with sodium borohydride (24 mg, 0.63 mmol) for an additional 2 h. LC-MS showed the reaction was complete. The reaction was quenched with water and extracted with ethyl acetate/tetrahydrofuran, dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to afford 192 mg of desired product as a white solid, which was pure enough for next step without further purification.

Provenance & Evidence