反应详情

To a suspension of N-(5-hydroxy-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide (0.553 g, 2.69 mmol) and isopropyl 4-imidazolecarboxylate (0.290 g, 1.88 mmol), which can be prepared as described in Example 1, in THF (10 mL) at 0° C. is added triphenylphosphine (1.415 g, 5.39 mmol) and dimethyl azodicarboxylate (40% wt. in toluene, 1.97 g, 5.39 mmol). The cooling bath is removed and the mixture is stirred for 15 min. Water is added and the mixture is extracted with ethyl acetate. The organic phase is dried over sodium sulfate, filtered and concentrated. The resulting residue is purified by silica gel chromatography (elution with dichloromethane-methanol mixtures) to give 3-(6-acetylamino-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester; MS: (ESI) m/z 342.2 (M+H)+; 1H NMR (400 MHz, MeOD) δ ppm 1.39 (d, J=6.3 Hz, 3 H), 1.40 (d, J=6.0 Hz, 3 H), 1.71-1.82 (m, 1 H), 1.83-1.92 (m, 1 H), 2.16 (s, 3H), 2.17-2.30 (m, 2 H), 2.86 (ddd, J=16.9, 8.3; 5.6 Hz, 1 H), 3.00 (dt, J=16.9, 5.6 Hz, 1 H), 5.25 (sept., J=6.3 Hz, 1 H), 6.30 (t, J=5.3 Hz, 1 H), 6.93 (d, J=8.3 Hz, 1 H), 7.34-7.36 (m, 2 H), 7.53 (d, J=1.8 Hz, 1 H), 7.74 (d, J=1.0 Hz, 1 H).

1. customcan be prepared
2. customThe cooling bath is removed
3. additionWater is added
4. extractionthe mixture is extracted with ethyl acetate
5. dry with materialThe organic phase is dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe resulting residue is purified by silica gel chromatography (elution with dichloromethane-methanol mixtures)