[CH2:1]1[CH2:11][C:9](=[O:10])[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.[CH2:12]([O:14][C:15](=[O:23])[N:16]([CH2:20][CH2:21]Br)[CH2:17][CH2:18]Br)[CH3:13].[H-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[O:10]=[C:9]1[C:11]2([CH2:21][CH2:20][N:16]([C:15]([O:14][CH2:12][CH3:13])=[O:23])[CH2:17][CH2:18]2)[CH2:1][CH2:2][C:3]2[C:8]1=[CH:7][CH:6]=[CH:5][CH:4]=2
To a stirred solution of α-tetralone (289 mg, 1.98 mmol) and bis-(2-bromo-ethyl)-carbamic acid ethyl ester (600 mg, 1.98 mmol) in DMF (2 mL) at 50° C. was added NaH (119 mg, 4.95 mmol) by small portions. After being stirred at 50° C. for 12 h, the reaction was cooled to 25° C. The reaction mixture was diluted with 15 mL of ethyl acetate and washed twice with 10 mL of water, dried over Na2SO4 and concentrated. The crude product was purified via flash chromatography (gradient of 85:15 to 60:40 heptane/ethyl acetate over 20 min) to give the title compound (85 mg, 0.296 mmol) as a white solid. MS calculated for C17H22NO3 288.4. found (ESI) m/z 288.7 (M+H)+, retention time 1.58 min.
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