[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][O:12][C:13]1[CH:29]=[CH:28][C:16]([CH2:17][N:18]2[CH2:23][CH2:22][CH:21]([C:24](OC)=[O:25])[CH2:20][CH2:19]2)=[CH:15][CH:14]=1.CO.[Cl-].[Na+]>C1(C)C=CC=CC=1>[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][N:18]2[CH2:23][CH2:22][CH:21]([CH:24]=[O:25])[CH2:20][CH2:19]2)=[CH:28][CH:29]=1A 1.5 M solution of diisobutylaluminium hydride in toluene (3.12 ml, 4.68 mmol) was added dropwise under argon at −78° C., in the course of 30 minutes, to a solution of methyl 1-(4-methoxybenzyl)piperidine-4-carboxylate (1.23 g, 4.68 mmol) in toluene (30 ml), and stirring was then carried out for 30 min at that temperature. Methanol (15 ml) was then added dropwise in such a manner that the internal temperature remained at −78° C., before the mixture was then slowly warmed to room temperature. Saturated sodium chloride solution (20 ml) was added to the reaction mixture, and the suspension was filtered through sea sand. The organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography with cyclohexane/ethyl acetate (1:3).
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