Acetic Acid → HCID 10390885, compound

Participants

Reaction Steps

To a room temperature solution of propionaldehyde (40.6 μL 0.56 mmol) and COMPOUND 27 (250 mg; 0.56 mmol) in 1,2-dichloroethane was added sodium triacetoxy borohydride (380 mg; 1.79 mmol) and acetic acid (31.9 μL; 0.56 mmol). The reaction mixture was stirred overnight then was washed with saturated sodium bicarbonate, followed by water. The organic phase was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. Column chromatography eluting with 5% methanol in dichloromethane gave COMPOUND 73 (169 g; 62% yield). Purity (HPLC-215 nm): >99%; Optical purity (Chiral HPLC-215 nm): >99%. 1H NMR (400 MHz, CD3OD) δ 0.99 (t, J=7.91 Hz, 2H), 1.10-1.16 (m, 3H), 1.28-1.33 (m, 4H), 1.61-1.65 (m, 4H), 1.75-1.79 (m, 4H), 1.83-1.90 (m, 4H), 2.97-3.01 (m, 2H), 3.13-3.15 (m, 2H), 3.17-3.28 (m, 8H), 3.42-3.46 (m, 2H), 3.52-3.54 (m, 1H), 5.08 (s, 1H) 7.24-7.29 (m, 3H), 7.48-7.51 (m, 3H), 7.55-7.57 (m, 1H), 7.62 (d, J=7.42 Hz, 1H). Found: C, 56.59; H, 7.89; N, 8.25. C31H46N4O×4.3HCl×0.6H2O has C, 56.56; H, 7.89; N, 8.51%. [α]D16=+14.5 deg [c 0.50, MeOH].

Provenance & Evidence