Acetaldehyde → HCID 131728473, compound

Participants

Reaction Steps

Acetaldehyde (0.151 g, 3.4 mmol) was added to a solution of Example 92k (0.330 g, 0.68 mmol) in MeOH (10 mL) at 0° C. TFA (0.08 g, 0.68 mmol) was then added and stirring continued for 2 h. The reaction mixture was brought to room temperature, treated with sodium cyanoborohydride (0.108 g, 1.7 mmol) and allowed to stir for 4 h. It was concentrated, treated with aqueous sodium bicarbonate solution, water and extracted ethyl acetate. The organic layer was washed with water, brine, dried, concentrated and purified using flash chromatography to obtain the title compound. Yield: 0.80 g, (51%); 1H NMR (CDCl3): δ 1.20 (t, 2H, CH2), 1.70 (t, 2H, CH2), 1.80 (t, 4H, 2CH2), 2.70 (s, 3H, CH3), 2.80 (s, 2H, CH2), 2.90 (m, 2H, CH2), 3.40 (q, 2H, CH2), 3.80 (t, 2H, CH2), 3.9 (s, 3H, OCH3), 4.8 (s, 2H, CH2), 6.8 (s, 2H, Ar), 8.10 (s, 1H, Ar), 8.4 (s, 1H, Ar); MS: m/e (ES−) 506 (M−1).

Provenance & Evidence