HCID 69832881, compound → HCID 69832857, compound

Participants

Reaction Steps

A solution of cis-4-(benzyl-ethoxycarbonyl-amino)-6,7-dimethoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid benzyl ester (Example 4) (1.0 g, 1.9 mmol) in ethanol (20 mL) was placed in a Parr bottle, charged with 10% palladium on carbon (100 mg), and agitated under 50 psi of hydrogen gas on a Parr shaker for 2 h. The mixture was then filtered through a bed of Celite®, eluting with ethyl acetate, and the filtrate concentrated in vacuo. The residue was purified by silica gel chromatography using 30% ethyl acetate/hexanes as eluent to afford 660 mg of the desired final product (89%): MS m/z 204 (M+−PhCH2NHCO2Et−H2+1); 1H NMR (CDCl3) δ1.12 (d, 3H), 1.17 (t, 3H), 3.65 (s, 3H), 3.8 (s, 3H), 6.10 (C5, s, 1H), 6.44 (C8, s, 1H), 7.1-7.3 (m, 5H).

Provenance & Evidence