Aluminium lithium hydride → HCID 57781143, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(3,3-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinolin-4-yl)-3H-imidazole-4-carboxylic acid methyl ester (200 mg, 0.67 mmol) (Example 33c) in THF (20 mL) at −10° C. is added lithium aluminum hydride (56 mg, 1.47 mmol). After stirring for 5 min the reaction is placed at room temperature for 1 h, at which time the reaction is cooled to 0° C. and quenched by the consecutive addition of 9:1 THF/H2O (0.8 mL), 2M aqueous NaOH (0.92 mL), and H2O (0.6 mL). The reaction is then warmed to room temperature and diluted with THF (6 mL). After the addition of MgSO4 (900 mg), the heterogeneous mixture is stirred for 15 min and then filtered through a pad of Celite®. The pad of Celite® is washed with ethyl acetate and the combined filtrate is concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-hexanes-ethanol, 6.5:2.5:1 to 9:0.5:1.2) to furnish 4-(5-hydroxymethyl-imidazol-1-yl)-3,3-dimethyl-3,4-dihydro-2H-isoquinolin-1-one; MS (ESI) m/z 272.0 (M+H); 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.11 (s, 3 H), 1.42 (s, 3 H), 2.25 (br. s., 1 H), 4.61-4.93 (m, 2 H), 5.40 (s, 1 H), 5.73 (br. s., 1 H), 6.96 (s, 1 H), 7.32-7.37 (m, 1 H), 7.38 (s, 1 H), 7.46-7.56 (m, 2 H), 8.15-8.26 (m, 1 H).

Provenance & Evidence