Water → HCID 23019697, compound

HRID 1354188Notes

Reaction equation

HRID 1354188 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

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 23019628HCID 23019628, compound

Product 1

HCID 23019697HCID 23019697, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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.

Workup

  1. extractionAfter the extraction with chloroform
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe obtained residue was purified by the silica gel column chromatography (eluent: chloroform/methanol=100/3)

Sources & evidence

ORD record
ord-70d501ccbe264c9bbd9d3b792e6f4620
Source dataset
uspto-grants-2007_05
Patent number
US07223773B2

Reaction notes

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