Tert-Butylamine → HCID 67515804, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence