Diisopropylethylamine → HCID 59400104, compound

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Reaction Steps

To a solution of 1,2,3,4-tetrahydroquinolin-3-amine bis HCl salt (925 mg), diisopropylethylamine (4 mL), L-(+)mandelic acid (636 mg) and 4-dimethylaminopyridine (510 mg) in dimethylformamide (40 mL) was added HBTU (1.6 g). The mixture was stirred at room temperature for 48 hours before being poured into ethyl acetate (150 mL), washed with water (2×400 mL), dried over magnesium sulfate and evaporated to dryness. The crude product was purified by flash chromatography using a gradient (50-70% ethyl acetate in hexanes) to give (S)-2-hydroxy-2-phenyl-N—((R)-1,2,3,4-tetrahydroquinolin-3-yl)acetamide (310 mg) and (S)-2-hydroxy-2-phenyl-N—((S)-1,2,3,4-tetrahydroquinolin-3-yl)acetamide (360 mg) as white solids. 1H NMR (DMSO-d6) 400 MHz δ 7.79 (d, J=8 Hz, 1H), 7.41-7.25 (m, 5H), 6.91-6.85 (m, 2H), 6.51-6.45 (m, 2H), 6.25 (d, J=4.4 Hz, 1H), 5.76 (br s, 1H), 4.90 (d, J=5.2 Hz, 1H), 4.09-4.01 (m, 1H), 3.18-3.14 (m, 1H), 3.03-2.98 (m, 1H), 2.87-2.81 (m, 1H), 2.76-2.70 (m, 1H). LCMS m/e 283 (M+H).

Provenance & Evidence