Water → HCID 23019697, compound

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][N:13]3[C:18]([C:19]=2[CH3:20])=[C:17]([CH:21]2[CH2:23][CH2:22]2)[CH:16]=[C:15]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:14]3=[O:29])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+].O>C(O)C>[CH:21]1([C:17]2[CH:16]=[C:15]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:14](=[O:29])[N:13]3[C:18]=2[C:19]([CH3:20])=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([CH:1]([OH:3])[CH3:2])=[CH:5][CH:6]=2)[CH:11]=[CH:12]3)[CH2:22][CH2:23]1

Participants

Procedure

50 mg of ethyl 8-(4-acetylphenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (Example 3) was dissolved in 1 ml of ethanol. 9 mg of sodium borohydride was added to the obtained solution, and they were stirred at room temperature for 14 hours. Water was added to the reaction mixture. After the extraction with chloroform, the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by the silica gel column chromatography (eluent: chloroform/methanol=100/3) to obtain 35 mg of ethyl 1-cyclopropyl-8-[4-(1-hydroxyethyl)phenyl]-9-methyl-4-oxo-4H-quinolizine-3-carboxylate.