Triethylamine → Methyl-4-[(2S,4R)-1-acetyl-4-amino-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl]-3-methylbenzoate

Temperature

0 °C

Methyl 4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-3-methylbenzoate (for a preparation see Intermediate 97) (320 mg, 0.730 mmol) was added to a cold (ice bath) suspension of aluminium chloride (370 mg, 2.77 mmol) in dichloromethane (DCM) (4 mL). The reaction was stirred at approximately 0° C. for 30 min, then treated with a solution of methanol (0.320 mL) and triethylamine (1.230 mL, 8.82 mmol). The resulting mixture was stirred further at approximately 0° C. for 20 min then was diluted with EtOAc (25 mL) and a saturated NaHCO3 aqueous solution (25 mL). The reaction mixture was then filtered through celite and the insoluble residues were washed with EtOAc (15 mL) and a saturated NaHCO3 aqueous solution (15 ml). The filtered aluminum residues were suspended in MeOH and sonicated. The resulting suspension was filtered and the filtrate was concentrated in vacuo to give a white solid. This solid was loaded onto a 20 G SCX cartridge and eluted with MeOH then with 2M NH3 in MeOH. The ammonia fractions were combined and concentrated in vacuo to give methyl 4-[(2S,4R)-1-acetyl-4-amino-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl]-3-methylbenzoate (145 mg, 56%).

1. stirringThe resulting mixture was stirred further at approximately 0° C. for 20 min
2. filtrationThe reaction mixture was then filtered through celite
3. washthe insoluble residues were washed with EtOAc (15 mL)
4. customsonicated
5. filtrationThe resulting suspension was filtered
6. concentrationthe filtrate was concentrated in vacuo
7. customto give a white solid
8. washeluted with MeOH
9. concentrationconcentrated in vacuo

ORD record

ord-163548b4c45f46778ea0501ef4610358

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08580957B2