Acetic Acid → HCID 70162931, compound

Participants

Reaction Steps

To a solution of 5-(2-adamantan-1-yl-ethyl)-1-methyl-2-o-tolyl-1H-imidazole-4-carbaldehyde (Example 275, step b) (500 mg, 1.38 mmol) and 3-amino-benzoic acid benzyl ester (313 mg, 1.38 mmol) in 1,2-dichloroethane (5 ml) were added sodium triacetoxyborohydride (409 mg, 1.93 mmol) and then acetic acid (79 μl, 1.38 mmol). The suspension was stirred at room temperature for 2 h, then saturated sodium bicarbonate (40 ml) was added. The product was extracted with ethyl acetate (40 ml), the organic phase was washed with brine (40 ml), dried (MgSO4) and the filtrate was evaporated. The residue was purified by flash column chromatography (silica, hexane/ethyl acetate 1:1) to afford the product (725 mg, 92%). 1H NMR (300 MHz, CDCl3) 7.44-7.23 (12H, m), 6.91 (1H, m), 5.36 (2H, s), 4.50 (1H, br s), 4.24 (2H, s), 3.33 (3H, s), 2.61 (2H, m), 2.20 (3H, s), 2.00 (3H, br s), 1.77-1.57 (12H, m), 1.31 (2H, m).

Provenance & Evidence