[H-].[H-].[H-].[H-].[Li+].[Al+3].[Br:7][C:8]1[CH:9]=[C:10]([CH3:23])[C:11]([NH:14][C:15](=O)[CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:12][CH:13]=1.[OH-].[Na+].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[Br:7][C:8]1[CH:9]=[C:10]([CH3:23])[C:11]([NH:14][CH2:15][CH2:16][N:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)=[N:12][CH:13]=1Under an argon atmosphere 2 mL of a 1 M solution of LiAlH4 in THF are slowly added dropwise to a solution, cooled to 0° C., of 800 mg (2.68 mmol) N-(5-bromo-3-methyl-pyridin-2-yl)-2-pyrrolidin-1-yl-acetamide (Example 15b) in 10 mL THF and the reaction mixture is stirred for 3 h at this temperature. 20% NaOH is slowly added dropwise, solid K2CO3 is added to the suspension and this is stirred vigorously. The precipitate is filtered off, the filtrate is evaporated down and the residue is purified by chromatography (silica gel, EtOAc/MeOH/NH3 80:20:2).
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