Pyridine → HCID 87440141, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)- or (S)-3-(2,2-dimethyl-4-oxo-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid methyl ester (0.091 g, 0.299 mmol), which can be prepared as described in Example 13, and methoxyamine hydrochloride (0.076 g, 0.897 mmol) in methanol (2 mL) is added pyridine (0.24 g, 2.99 mmol) and the mixture is heated to 50° C. After 1.5 hours, the mixture is diluted with ethyl acetate and washed twice with aqueous copper sulfate, twice with 1:9 v/v aqueous ammonium hydroxide-saturated aqueous ammonium chloride, water, and brine. The organic layer is dried over MgSO4, filtered, and concentrated to furnish (R)- or (S)-3-{4-[(E)-methoxyimino]-2,2-dimethyl-1,2,3,4-tetrahydro-naphthalen-1-yl}-3H-imidazole-4-carboxylic acid methyl ester as a 19:1 ratio of geometric isomer without the need for further purification. 1H NMR (400 MHz, MeOD) δ ppm 0.94 (s, 3 H), 1.10 (s, 3 H), 2.52 (d, J=17.9 Hz, 1 H), 2.99 (d, J=17.9 Hz, 1 H), 4.03 (s, 3 H), 4.06 (s, 3 H), 6.65 (s, 1 H), 7.17-7.26 (m, 1 H), 7.41-7.49 (m, 2 H), 8.18-8.22 (m, 2 H), 8.27 (br. s., 1 H).

Provenance & Evidence