反应详情

The title compound was synthesized in two steps. First, methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (1.00 g, 5.58 mmol) was reacted with 2-naphthalenylmagnesium bromide (55 mL, 21 mmol) according to General Procedure 3. In this example, the 2-naphthalenylmagnesium bromide was first placed in a separate flask and the Et2O was blown off with N2. The residue was then dissolved in 50 mL THF, and added to the 4-oxo solution over 20 min via cannulae. The resulting exo-olefin ((E)-methyl 4-(naphthalen-2-ylmethylene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate) was converted to the title compound by hydrogenation according to General Procedure 6 (with 10% Pd/C). The crude product was used in the next step without further purification. 1H NMR (400 MHz, ACETONE-d6) δ ppm 2.16 (ddt, J=12.27, 8.77, 6.00, 6.00 Hz, 1H) 2.51-2.62 (m, 1H) 2.62-2.78 (m, 2H) 2.97 (d, J=7.61 Hz, 2H) 3.37-3.46 (m, 1H) 3.67-3.69 (m, 3 H) 6.27 (d, J=1.71 Hz, 1H) 7.40-7.52 (m, 3H) 7.73 (s, 1H) 7.81-7.91 (m, 3H) 10.47 (br. s, 1H).

1. customThe title compound was synthesized in two steps
2. customThe crude product was used in the next step without further purification