C(O)(=O)C.FC(F)(F)C(O)=O.[BH4-].[Na+].[CH3:14][N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][C:24]([CH:27](O)[C:28]#[CH:29])=[CH:23][CH:22]=2)[CH2:17][CH2:16]1>C(Cl)Cl>[CH3:14][N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][C:28]#[CH:29])=[CH:23][CH:22]=2)[CH2:17][CH2:16]1To a stirred mixture of glacial acetic acid (72 ml) and trifluoroacetic acid (8 ml), NaBH4 (79.1 mmol) is added slowly under nitrogen at −15° C. The solution of 1-[4-(4-methyl-piperazin-1-yl)-phenyl]-prop-2-yn-1-ol (1 1.3 mmol) in CH2Cl2 (80 ml) is added dropwise over 0.5 h and the mixture is stirred at room temperature for 1 h. The solvents are removed under reduced pressure and the residue is added to saturated sodium bicarbonate. The aqueous solution is extracted with CH2Cl2. The organic layer is washed with brine, dried over magnesium sulfate and evaporated down. The crude product is applied to silica gel column chromatography, which is eluted with following solvents: CH2Cl2 and 5% MeOH in CH2Cl2. The solvent of the latter effluent is removed by evaporation and dried in vacuo to afford the title compound. yield 86.8%, Rf=0.52 (CH2Cl2:MeOH=9:1).
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