[CH:1]([CH:3]1[C:15]2[CH:14]=[C:13]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)=[O:2].[BH4-].[Na+].C(NC1C=CC2C3C(=CC=CC=3)CC=2C=1)(OC(C)(C)C)=O.CC(OC)(C)C>CO.O.CCOC(C)=O.CC(O)=O>[OH:2][CH2:1][CH:3]1[C:15]2[CH:14]=[C:13]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2
9-Formyl-2-(Boc-amino)fluorene was suspended in 100 ml methanol and 2.0 g NaBH4 [52.9 mmol, 1.1 equiv with respect to the starting 2-(Boc-amino)fluorene] was added portion wise. The suspension that rapidly cleared up was magnetically stirred until the starting product disappeared for 4 h at room temperature [TLC, Rf=0.57, PE:MTBE (1:2)]. The reaction mixture was diluted with 300 ml H2O and acidified with 15 ml glacial HOAc to pH 5.0, and the precipitate was directly dissolved in 150 ml EtOAc. The organic phase was washed with 3×50 ml sat. NaHCO3 and 1×50 ml brine and dried over anhydrous Na2SO4. The solvent was rotary evaporated to give a solid, which could be used without further purification. The product was analyzed by NMR (13.1 g, 88% yield).
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