[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]12[CH2:15][CH2:14][CH:11]([CH2:12][CH2:13]1)[N:10]([C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)=O)[CH2:9][CH2:8]2.C(Cl)(Cl)Cl.CO.C(Cl)(Cl)Cl>C1COCC1>[N:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:16][N:10]1[CH:11]2[CH2:12][CH2:13][N:7]([CH2:15][CH2:14]2)[CH2:8][CH2:9]1To a stirred solution of lithium aluminum hydride (0.33 mL of 1M THF solution) at ambient temperature was added dropwise a solution of (1,4-diazabicyclo[3.2.2]non-4-yl)(pyridin-2-yl)methanone (120 mg, 0.52 mmol) in dry THF (2 mL). The resulting yellowish solution was stirred for 12 hours, quenched with water and aqueous NaOH, and filtered through diatomaceous earth. The filtrate was concentrated to give the product which was subjected to chromatography on silica gel eluting with an ammoniated-chloroform to 15% MeOH/chloroform gradient to give the title compound as a free base syrup (28.0 mg). MS (ES+) 218 (MH+).
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