[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([CH2:12][C:13]1[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH:18]=1)=O)C.C(OCC)(=O)C.O>C(OCC)C.O1CCCC1>[OH:9][CH2:10][CH2:12][C:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH:14]=1To a suspension of 0.66 g (17.5 mM) of lithium aluminum hydride in 100 ml of diethyl ether was added a solution of 4.719 g (17.521 mM) of tert-butyl 4-(ethoxycarbonylmethyl)-3,6-dihydro-2H-pyridine-1-carboxylate in 50 ml of tetrahydrofuran dropwise under ice-cooling and the mixture was stirred at room temperature for 1 hour. To this reaction mixture was added ethyl acetate with ice-cooling to decompose the excess lithium aluminum hydride. Then, water was added until a white precipitate had formed. The precipitate was filtered off with the aid of celite and the celite was washed with ethyl acetate. The filtrate and washes were pooled and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1) to provide the title compound.
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