[CH:1]([CH2:3][N:4]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6])=[O:2].[CH2:19]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C:32](O[BH-](OC(=O)C)OC(=O)C)(=[O:34])C.[Na+].[C:46](=O)([O-])O.[Na+]>O.C(Cl)Cl.C(O)(=O)C>[CH3:46][O:2][CH:1]([O:34][CH3:32])[CH2:3][N:4]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6].[CH:7]1([C:5]([N:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:3][CH2:1][N:29]2[CH2:30][CH2:31][N:26]([CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:27][CH2:28]2)=[O:6])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1A mixture of 0.3 g of Compound 1B, 0.2 mL of 1-benzylpiperazine, 0.14 mL of acetic acid, 0.38 g of sodium triacetoxyborohydride and 7 mL of methylene chloride was stirred at room temperature for 24 h. Afterwards, it was diluted with water, alkalinized with 5% aq. sodium hydrogencarbonate. The organic layer was separated, dried on sodium sulphate and evaporated to dryness in vacuo affording a crude, which was purified by flash chromatography (methylene chloride—methanol 9.5:0.5) affording 0.03 g (3.6% overall from Compound 1A) of the title product.
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