(Methoxycarbonylsulfamoyl)triethylammonium hydroxide → HCID 11023310, compound

Participants

Reaction Steps

4-Hydroxy-4-quinolin-2-yl-piperidine-1-carboxylic acid tert-butyl ester (3.16 g, 9.61 mmol) and (methoxycarbonylsulfamoyl)triethylammonium hydroxide, inner salt (5.00 g, 20.98 mmol) in benzene (60 mL) under N2 were refluxed for 3 hours. The solution was cooled to ambient temperature, diluted with water (50 mL) and the resulting mixture was stirred at ambient temperature for 10 minutes. The benzene layer was separated, washed with brine, dried over magnesium sulfate and concentrated onto silica gel; flash chromatography using an ethyl acetate/hexanes gradient gave 4-quinolin-2-yl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (1.65 g, 55%) as a yellow oil. 1H NMR CDCl3 δ 8.09 (d, J=9 Hz, 1H), 8.03 (d, J=8 Hz, 1H), 7.76 (d, J=8 Hz, 1H), 7.70-7.63 (m, 1H), 7.56 (d, J=9 Hz, 1H), 7.51-7.44 (m, 1H), 6.69-6.63 (m, 1H), 4.21-4.14 (m, 2H), 3.68 (t, J=6 Hz, 1H), 2.87-2.80 (m, 2H), 1.48 (s, 9H).

Provenance & Evidence