[H-].[Na+].[Br:3][C:4]1[C:5]([CH2:19][CH3:20])=[C:6]([CH2:10]P(=O)(OCC)OCC)[CH:7]=[CH:8][CH:9]=1.O=[C:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1.O>O1CCCC1>[Br:3][C:4]1[C:5]([CH2:19][CH3:20])=[C:6]([CH:10]=[C:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]2)[CH:7]=[CH:8][CH:9]=1
To a suspension of NaH (0.155 g, 3.88 mmol) in Tetrahydrofuran (THF) (30 mL) was added diethyl [(3-bromo-2-ethylphenyl)methyl]phosphonate (D135) (1 g, 2.98 mmol) at 0° C. The reaction solution was warmed to room temperature and stirred for 1 hour. The reaction solution was cooled to 0° C. again and 1,1-dimethylethyl 4-oxo-1-piperidinecarboxylate (0.713 g, 3.58 mmol) was added. The reaction solution was warmed to room temperature and stirred overnight. Water was added and extracted with ethyl acetate, the organic phases were dried over sodium sulphate, concentrated and purified by ISCO column chromatography to afford 1,1-dimethylethyl 4-[(3-bromo-2-ethylphenyl)methylidene]-1-piperidinecarboxylate (D136) (0.73 g). MS (ES): C19H26BrNO2 requires 379.1. found 324.1 (M+H+-56).
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