C([N:8]1[CH2:13][CH2:12][Si:11]([CH3:15])([CH3:14])[CH2:10][CH2:9]1)C1C=CC=CC=1.[ClH:16].C(OCC)C>C(O)C>[ClH:16].[CH3:14][Si:11]1([CH3:15])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1To a solution of 3 (2.3 g, 10.5 mmol) in ethanol (EtOH), 6 N HCl (10.5 mmol) is added and the solvent is removed under reduced pressure. The reaction mixture is co-evaporated with EtOH (2×10 mL) and recrystallized from EtOH-diethyl ether. To a slurry of Pd/C in EtOH, an ethanolic solution of the HCl salt is added dropwise and stirred at 25° C. under hydrogen atmosphere for 20 h. The reaction mixture is filtered through celite, washed with 2×20 mL of Methanol. The filtrate is concentrated under reduced pressure to give a viscous oil which is titrated with diethyl ether to obtain the product 4 as a white solid (950 mg) in 70% yield. This compound was previously documented in WO 2006/066872.
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