Acetaldehyde → HCID 131728453, compound

Participants

Reaction Conditions

Reaction Steps

Acetaldehyde (0.21 mL, 3.80 mmole) was added to a solution of Example 66k (0.370 gm, 0.76 mmol) in dry methanol (15 mL) followed by the addition of trifluoro-acetic acid (0.06 mL, 0.76 mmol). The reaction mixture was stirred at 0° C. for 2 h, allowed to come to room temperature, treated with sodium cyanoborohydride (0.119 g, 1.9 mmol), and stirred overnight. It was concentrated, treated with 10% aqueous sodium bicarbonate solution, water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried, concentrated and purified using flash chromatography (silica gel, methanol/chloroform) to obtain the title compound as a white solid. Yield: 0.3 g, (76.72%); 1H NMR (CDCl3): δ 2.15 (t, 3H, CH3), 2.45-2.55 (m, 6H, 3CH2), 2.70 (s, 3H, CH3), 3.40 (q, 2H, CH2), 3.50 (t, 2H, CH2), 3.70-3.80 (m, 4H, CH2), 3.95 (s, 3H, OCH3), 4.70 (s, 2H, CH2), 6.55 (s, 1H, Ar), 6.70 (s, 1H, Ar), 8.10 (s, 1H, Ar), 8.45 (s, 1H, Ar); MS: m/e (CI+) 511 (M−CH3).

Provenance & Evidence