[CH2:1]([O:4][CH3:5])[C:2]#[CH:3].[CH2:6]([Li])[CH2:7]CC.CCCCCC.[CH3:17][N:18]([CH3:32])[C:19]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]1.[Br-].[Li+].C(I)C>O.CS(C)=O.C1COCC1>[CH2:6]([O:25][C:22]1([C:3]#[C:2][CH2:1][O:4][CH3:5])[CH2:23][CH2:24][C:19]([N:18]([CH3:32])[CH3:17])([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:20][CH2:21]1)[CH3:7]Methyl propargyl ether (1.47 g, 21.0 mmol) dissolved in abs. THF (15 mL) was added in drops to a 2.5 M solution of butyl lithium in hexane (8.4 mL, 21.0 mmol) at −30° C. in argon. A solution of 4-dimethylamino-4-phenylcyclohexanone (4.34 g, 20.0 mmol) in abs. THF (20 mL) and lithium bromide (0.87 g, 10 mmol) dissolved in abs. THF (2.5 mL) was then added at −30° C. The reaction mixture was heated to −5° C., mixed in drops with a solution of ethyl iodide (4.68 g, 30 mmol) in abs. DMSO (30 mL) and stirred for 2 h at 50° C. For work up of the reaction mixture water (30 mL) was added with ice bath cooling and extracted with cyclohexane (4×50 mL). The organic phase was washed with 20% ammonium chloride solution, dried over Na2SO4 and concentrated to low volume in a vacuum. The remaining residue was purified by flash chromatography with CHCl3/MeOH (20:1).
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