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

Participants

Reaction Steps

To a solution of XXII (6.0 g, 24.56 mmol) in 150 mL of MeOH was added acetic acid (18 mL). The mixture was bubbled with argon for 15 min, then palladium hydroxide (20% palladium on carbon, 1.2 g) was added to the flask. The resulting suspension was subjected to hydrogenation under 45 psi for 16 h before filtered. The filtrate was concentrated and the residue was dissolved in CH2Cl2. The resulting CH2Cl2 solution was washed with saturated NaHCO3, dried over Na2SO4 and concentrated. The residue was purified through silica gel to give (1,2,3,4-tetrahydro-quinoline-3-yl)-carbamic acid tert-butyl ester XXIII (4.2 g, 68%).

Provenance & Evidence