Acetic Acid → Boc-3-amino-1,2,3,4-tetrahydroquinoline

Participants

Reaction Steps

To a solution of 3-quinolinylcarbamic acid, 1,1-dimethylethyl ester (6.0 g, 24.56 mmol) in MeOH (150 mL) was added acetic acid (18 mL). The mixture was bubbled with argon for 15 min, then palladium hydroxide (20 weight % palladium on carbon) (1.2 g) was added. The resulting suspension was subjected to hydrogenation under 45 psi of pressure for 16 h, then filtered. The filtrate was concentrated and the residue taken in CH2Cl2. The resulting CH2Cl2 solution was washed with saturated aqueous NaHCO3, saturated aqueous NaCl, dried (Na2SO4) and concentrated. The residue was chromatographed (silica gel) eluting with EtOAc (0 to 50%) in hexanes to give 1A (4.6 g, 75% yield) as a white solid.

Provenance & Evidence