Acetic Acid → HCID 86755984, compound

Participants

Reaction Steps

A solution of cis-(3,5-bis-trifluoromethyl-benzyl)-(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl)-carbamic acid methyl ester (Example 67) (34 mg, 0.067 mmol), acetic acid (4 μL, 0.067 mmol), butyraldehyde (17 μL, 0.34 mmol), and sodium triacetoxyborohydride (71 μL, 0.34 mmol) in anhydrous dichloroethane (1 mL) were stirred at room temperature overnight. Water (5 mL) was added, the aqueous phase made basic with potassium carbonate, and the mixture was extracted with ethyl acetate (3×10 mL). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. Purification by silica gel chromatography using 0-15% ethyl acetate/hexanes as eluent afforded 32 mg of the title compound (82%):MS m/z 563 (M+ +1); 1H NMR (CDCl3) δ 6.31 (C8, s, 1H), 3.64 (CO2Me, s, 3H), 1.20 (C2-Me, d, 3H, J=6.3 Hz). The hydrochloride salt was prepared by treating an ethereal solution of the free base with an ethereal solution of HCl. Hydrochloride salt:1H NMR (CDCl3) δ 3.83 (CO2Me, s, 3H), 1.20 (C2-Me, d, 3H, J=6.4 Hz).

Provenance & Evidence