methyl 1-oxido-5,6,7,8-tetrahydroquinolin-1-ium-5-carboxylate

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 5,6,7,8-tetrahydroquinoline-5-carboxylate-1-oxide (2.05 g, 9.89 mmol) and t-butyl amine (5.22 mL, 49.5 mmol) were dissolved in benzotrifluoride (50 ml) and cooled with an ice bath. The p-toluenesulfonic anhydride (6.46 g, 19.79 mmol) was added portionwise keeping the reaction's internal temperature below 5° C. The reaction was monitored and after 10 mins when the LC-MS showed M+1=263 and 207 (M-56) at 1.20 indicating formation of intermediate methyl 2-(tert-butylamino)-5,6,7,8-tetrahydroquinoline-5-carboxylate. TFA (10 mL) was then added to the reaction mixture and heated at 70° C. for 5 hrs. The reaction was cooled and evaporated to dryness. The residue was taken up with water and the pH was adjusted to ˜8 with 5N NaOH. The reaction was extracted 2× with DCM. The combined DCM layers were washed with brine and dried over Na2SO4, filtered and evaporated to dryness. The residue was chromatographed through an 80 g ISCO Redi-sep column and eluted with solvent system of 5% (10% NH4OH in MeOH)/DCM to yield the title compound: LC-MS: M+1=207. cooled with an ice bath the reaction's internal temperature below 5° C The reaction was cooled evaporated to dryness The reaction was extracted 2× with DCM The combined DCM layers were washed with brine dried over Na2SO4 filtered evaporated to dryness The residue was chromatographed through an 80 g ISCO Redi-sep column eluted with solvent system of 5% (10% NH4OH in MeOH)/DCM

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 5,6,7,8-tetrahydroquinoline-5-carboxylate-1-oxide (2.05 g, 9.89 mmol) and t-butyl amine (5.22 ml, 49.5 mmol) were dissolved in benzotrifluoride (50 ml) and cooled with an ice bath. The p-toluenesulfonic anhydride (6.46 g, 19.79 mmol) was added portionwise keeping the reaction's internal temperature below 5° C. The reaction was monitored and after 10 mins. when the LC-MS showed M+1=263 and 207 (M-56) at 1.20 indicating formation of intermediate methyl 2-(tert-butylamino)-5,6,7,8-tetrahydroquinoline-5-carboxylate. Trifluoroacetic acid (10 ml) was then added to the reaction mixture and heated at 70° C. for 5 hrs. The reaction was cooled and evaporated to dryness. The residue was taken up with water and the pH was adjusted to pH ˜8 with 5N NaOH. The reaction was extraction with DCM 2×. The combined DCM layers were washed with brine and dried over Na2SO4, filtered and evaporated to dryness. The residue was chromatographed through a 80 g ISCO Redi-sep column and eluted with solvent system of 5%(10% NH4OH in MeOH)/DCM to yield methyl 2-amino-5,6,7,8-tetrahydroquinoline-5-carboxylate. 1H-NMR (600 MHz, CDCl3): δ ppm 7.27 (d, J=8.3 Hz, 1H), 6.35 (d, J=8.3 Hz, 1H), 4.40 (b, 2H), 3.73 (s, 3H), 3.70 (t, J=6.9 Hz, 1H), 2.68-2.82 (m, 2H) 2.12-2.17 (m, 1H), 1.93-2.12 (m, 2H), 1.81-1.86 (m, 1H); LC-MS: M+1=207; cooled with an ice bath the reaction's internal temperature below 5° C The reaction was cooled evaporated to dryness extraction with DCM 2× The combined DCM layers were washed with brine dried over Na2SO4 filtered evaporated to dryness The residue was chromatographed through a 80 g ISCO Redi-sep column eluted with solvent system of 5%(10% NH4OH in MeOH)/DCM