Water → HCID 59277719, compound

Participants

Reaction Steps

LiAlH4 (26 mg, 0.68 mmol) is carefully added to a solution of 3-(1-benzoyl-3,3-dimethyl-1,2,3,4-tetrahydro-quinolin-4-yl)-3H-imidazole-4-carboxylic acid methyl ester (101 mg, 0.26 mmol) in THF (10 mL) at 0° C. The resulting mixture is warmed up to room temperature. After overnight, NaF and water are added at 0° C. Then the reaction mixture is warmed up to room temperature and stirred until the grey suspension turned to off white color. The mixture is filtered and the filtrate is concentrated and taken up into ethyl acetate and washed with brine, and dried over anhydrous sodium sulfate. After concentration, the residue is purified by flash chromatography and gives the title compound (23 mg, 34.5% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.81 (s, 3 H), 1.08 (s, 3 H), 2.68 (br. s., 1 H), 2.97 (d, J=12.1 Hz, 1 H), 3.19 (d, J=12.1 Hz, 1 H), 4.22 (br. s., 1 H), 4.73 (s, 2 H), 5.11 (s, 1 H), 6.54-6.61 (m, 2 H), 6.87 (s, 1 H), 6.92 (d, J=7.3 Hz, 1 H), 7.08 (t, J=8.3 Hz, 1 H), 7.28 (s, 1 H). HRMS: calculated for C15H20N3O: 258.1606. Found: 258.1615.

Provenance & Evidence