[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([NH2:14])[CH:5]=[CH:4][C:3]1=2.[CH2:16]([Li])[CH2:17][CH2:18][CH3:19].ICCCC.[Cl-].[Na+]>O1CCCC1>[CH2:16]([NH:14][C:6]1[CH:5]=[CH:4][C:3]2[C:2]([CH3:15])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]=2[CH:7]=1)[CH2:17][CH2:18][CH3:19]A solution of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-ylamine (1) (0.3 g, 1.5 mmole) in 30 mL tetrahydrofuran (THF) was cooled to −78° C. and 2.5 M n-butyllithium solution (0.6 mL) was added dropwise. The reaction mixture was allowed to warm to 0° C. over a one hour period. Iodobutane (0.171 mL) was added at 0° C. and the reaction mixture was stirred at room temperature for 15 hours. The reaction mixture was then poured into 50 mL of a saturated aqueous sodium chloride solution and extracted with three portions of 50 mL of ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to provide a brown oil. The product was purified by flash chromatography (SiO2, 5% ethyl acetate/hexanes) to provide 143 mg (37%) of butyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine (7) as a pale yellow oil.
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