Tert-Butylamine → HCID 67515804, compound

Temperature

70 °C

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.

1. temperaturecooled with an ice bath
2. customthe reaction's internal temperature below 5° C
3. temperatureThe reaction was cooled
4. customevaporated to dryness
5. extractionThe reaction was extracted 2× with DCM
6. washThe combined DCM layers were washed with brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. customevaporated to dryness
10. customThe residue was chromatographed through an 80 g ISCO Redi-sep column
11. washeluted with solvent system of 5% (10% NH4OH in MeOH)/DCM

ORD record

ord-e06ce2814c184fe1b887454a2e8eee72

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09062070B2