Sodium borohydride → HCID 86592231, compound

Participants

Reaction Steps

To a solution of cis-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-2-(2-ethoxycarbonyl-cyclopropyl)-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid isopropyl ester (Example 53) (100 mg, 0.14 mmol) in refluxing methanol (40 ml) was added sodium borohydride (1.0 g) in portions, and the resulting mixture was heated to reflux for an additional 30 min. The cooled reaction was concentrated and the residue was partitioned between ethyl acetate and 2N HCl. The aqueous layer was extracted again with ethyl acetate and the combined extracts were dried (MgSO4), filtered and concentrated. The residue was chromatographed with 15-20% ethyl acetate/hexane to afford the title product (55 mg). MS m/z 657.2 (M+); 1H NMR (CDCl3) δ 3.8 (s, 3H), 3.9 (q, 1H), 7.1 (s, 1H), 7.5 (s, 2H), 7.7 (s, 1H).

Provenance & Evidence