Di-tert-butyl dicarbonate → HCID 67690717, compound

Participants

Reaction Steps

To a solution of trans-4-(2-azidomethylphenyl)methylcarbonylamino-5,7-dichloro-2-methoxycarbonyl-1,2,3,4-tetrahydroquinoline (0.3 g, 0.67 mmol) in ethyl acetate (30 ml) was added ditertiary-butyldicarbonate (0.22 g, 1.0 mmol) and 10% palladium on carbon and this mixture was hydrogenated under 50 psi pressure for 18 hours. The mixture was filtered and the solvent was removed under vacuum to yield the crude product, which was purified by flash chromatography (using ethyl acetate in hexane as eluent) followed by recrystallisation from ethyl acetate/hexane to give the title compound, m.p. 224°-225° C.; δ (360 MHz, DMSO) 1.38 (1H, ddd, J=13.2, 12.6 and 3.8 Hz, CHACHBHCCHD), 2.18 (1H, dm, J=13.2 Hz, CHACHBHCCHD), 3.50 (2H, s, NHCOCH2Ar), 3.73 (3H, s, CO2CH3), 3.95 (1H, dd, J=12.6 Hz, CHACHBHCCHD), 4.17 (2H, d, J=5.7 Hz, ArCH2NH), 5.00 (1H, m, CHACHBHCCHD), 6.70 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.87 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.92 (1H, s, ArNH), 7.19 (4H, m, ArH), 8.50 (1H, d, J=6.9 Hz, CHDNHCOCH2); m/e (EI+) 522 (M+1).

Provenance & Evidence