4-Nitrobenzenesulfonyl chloride → Tert-butyl 1-(4-nitrophenylsulfonyl)-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 1,2,3,4-tetrahydroquinolin-3-ylcarbamate (3.03 g, 12.2 mmol) and 4-nitrobenzene-1-sulfonyl chloride (2.99 g, 13.5 mmol) in 1,2-dichloroethane (60 mL) was added diisopropylethylamine (6.6 mL, 4.90 g, 37.9 mmol). The mixture was stirred at 75° C. for 15 hours. The mixture was quenched by addition of saturated aqueous sodium bicarbonate (80 mL) and extracted with dichloromethane (3×50 mL). The combined organic layers were washed with water (2×10 mL), dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by chromatography on silica gel (30% EtOAc/hexane) to give tert-butyl 1-(4-nitrophenylsulfonyl)-1,2,3,4-tetrahydroquinolin-3-ylcarbamate (4.6 g).

Provenance & Evidence