1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 19793367, compound

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Reaction Steps

To a mixture of 2 g (10.6 mmol) of 1-carbomethoxy-3,4-dihydronaphthalene, from Step 1 of Example 46, and 2.08 g (10.6 mmol) of 2-(3-nitrophenyl)-1-nitroethane, from Step 2, in 1 mL of acetonitrile was added 0.2 mL of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The reaction mixture was stirred at ambient temperature for 0.5 h and then diluted with ethyl acetate. The reaction mixture was washed with 2N aqueous hydrochloric acid solution. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give 3.96 g (97% yield) of the title compound as a mixture of diastereomers which was taken on without purification to the next step; MS DCI-NH3M/Z: 402 (M+NH4)+ ; 1H NMR (CDCl3) δ1.52-1.86 (1H, m), 2.1-2.35 (1H, m), 2.42-2.65 (1H, m), 2.78- 3.15 (2H, m), 3.2-3.33 (1H, m), 3.38-3.55 (1H, m). 3.78-3.81 (3H, s), 3.91-4.18 (1H, m), 4.68-4.88 (1H, m), 7.12-7.42 (4H, m), 7.48-7.58 (2H, m), 8.01-8.18 (2H, m).

Provenance & Evidence