Acetic Acid → HCID 59400150, compound

Participants

Reaction Steps

To a solution of (S)-2-hydroxy-2-phenyl-N—((S)-1,2,3,4-tetrahydroquinolin-3-yl)acetamide (355 mg, 1.26 mmol) in 1,2-dichloroethane (20 mL) was added 4-fluorobenzaldehyde (160 μL, 1.51 mmol) followed by glacial acetic acid (86 μL) and sodium triacetoxyborohydride (533 mg, 2.51 mmol). The reaction was stirred at room temperature for 16 hours. The reaction was diluted with DCM (20 mL) and quenched by addition of water (20 mL). The organic layer was separated and the aqueous layer was once again extracted with DCM (20 mL). The combined organic extracts were washed with water (2×50 mL) and brine (50 mL), dried over anhydrous sodium sulfate and evaporated to dryness. The crude product was purified by flash chromatography using a gradient (20-40% EtOAc in hexanes). The desired product (S)—N—((S)-1-(4-fluorobenzyl)-1,2,3,4-tetrahydroquinolin-3-yl)-2-hydroxy-2-phenylacetamide was obtained as a beige solid (351 mg, 72% yield). 1H NMR (DMSO-d6) 400 MHz δ 7.67 (d, J=7.8 Hz, 1H), 7.39-7.34 (m, 2H), 7.33-7.22 (m, 5H), 7.12-7.07 (m, 2H), 6.96-6.90 (m, 2H), 6.58-6.52 (m, 2H), 6.07 (d, J=5.1 Hz, 1H), 4.91 (d, J=4.7 Hz, 1H), 4.45 (d, J=16.8 Hz, 1H for AB system), 4.41 (d, J=16.4 Hz, 1H for AB system), 4.24-4.15 (m, 1H), 3.34 (ddd, J=11.3, 3.5, 1.2 Hz, 1H), 3.22 (dd, J=11.0, 7.0 Hz, 1H), 2.95 (dd, J=15.7, 4.7 Hz, 1H), 2.80 (dd, J=16.0, 7.8 Hz, 1H). LCMS m/e 391 (M+H).

Provenance & Evidence