[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]1[O:12][C:11](=[O:19])[C:10]([N:20]3[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[N:21]3)=[CH:9][C:8]2=1.Cl.CO>O1CCCC1>[OH:19][CH2:11][CH:10]([N:20]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[N:21]1)[CH2:9][C:8]1[C:7]2[C:16](=[CH:17][CH:18]=[C:5]([O:4][CH3:3])[CH:6]=2)[N:15]=[CH:14][C:13]=1[OH:12]Sodium borohydride (179 mg, 4.73 mmol, 8.0 eq) is added at 0° C. to a stirred solution of 6-methoxy-3-(4-nitro-pyrazol-1-yl)-1-oxa-9-aza-phenanthren-2-one (200 mg, 0.59 mmol, 1.0 eq) in tetrahydrofuran (50 mL). After 2 hours stirring at 0° C., the reaction mixture is cautiously acidified to pH=1 with a 4N hydrochloric acid aqueous solution. Tetrahydrofuran is evaporated and the residue is extracted with ethyl acetate (3×40 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a residue that is purified by column chromatography (silica gel, eluent: petroleum ethyl acetate:methanol, 20:1, v/v) to afford 4-[3-hydroxy-2-(4-nitro-pyrazol-1-yl)-propyl]-6-methoxy-quinolin-3-ol as a white solid (170 mg, 84% yield).
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