HCID 86757538, compound → HCID 86757537, compound

Participants

Reaction Steps

To a solution of cis-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-6,7-bis-hydroxymethyl-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (Example 27A) (100 mg, 0.17 mmol) in 25 ml anhydrous dichloromethane was added pyridinium chloro-chromate (100 mg, 0.46 mmol) and the resulting mixture was stirred at room temperature for 24 h. The reaction mixture was poured into a separatory funnel, washed with H2O and sat NaHCO3, dried and concentrated. The crude material was chromatographed on silica gel (30-35% ethyl acetate:hexane) to afford cis-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-2-methyl-8-oxo-3,4,6,8-tetrahydro-2H-furo[3,4-g]quinoline-1-carboxylic acid ethyl ester (Example 29) MS m/z 574 (M+); 1H NMR (CDCl3) δ3.8 (s, 3H), 7.5 (s, 1H), 7.8 (s, 1H) and cis-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-2-methyl-6-oxo-3,4,6,8-tetrahydro-2H-furo[3,4-g]quinoline-1-carboxylic acid ethyl ester (Example 30) MS m/z 575 (M+); 1H NMR (CDCl3) δ1.1 (d, 3H), 3.8 (s, 3H), 7.0 (s, 1H), 8.0 (br, 1H).

Provenance & Evidence