Acetaldehyde → HCID 131728516, compound

Participants

Reaction Conditions

Reaction Steps

Acetaldehyde (0.1 ml, 2.35 mmol) was added to a cooled solution of Example 198k (0.2 g, 0.47 mmol) in dry methanol (15 mL). Subsequently TFA (0.036 ml, 0.47 mmol) was added and the reaction mixture was stirred for 2 h. at 0° C. NaBH3CN (0.075 g, 1.17 mmol) was added and the reaction mixture was stirred for 15 h at room temperature. It was treated with a 10% aqueous sodium bicarbonate solution (1 mL) and the solid that precipitated was filtered, washed with water, dried and purified using flash chromatography (silica gel, methanol/chloroform) to obtain the title compound as a white solid. Yield: 0.150 g, (76.53%); 1H NMR (DMSO-d6): δ 1.05 (t, 6H, 2CH3), 2.55 (q, 4H, 2CH2), 2.70 (s, 3H, CH3), 3.55 (s, 2H, CH2), 4.00 (s, 3H, OCH3), 4.70 (s, 2H, CH2), 7.39 (s, 1H, Ar), 7.50 (s, 1H, Ar), 8.10 (s, 1H, Ar), 8.50 (s, 1H, Ar); MS: m/e (ES+) 438 (M+1).

Provenance & Evidence