Methanol → HCID 19364860, compound

HRID 850803Notes

Reaction equation

HRID 850803 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:15]3=[C:16]([C:18](=[O:21])[CH:19]=[CH:20][N:14]3[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]2=3)[CH:17]=1)=O.[H-].C([Al+]CC(C)C)C(C)C.CO.O>C(Cl)Cl>[OH:2][CH2:3][C:5]1[CH:6]=[C:7]2[C:15]3=[C:16]([C:18](=[O:21])[CH:19]=[CH:20][N:14]3[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]2=3)[CH:17]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 21252858HCID 21252858, compound

Product 1

HCID 19364860HCID 19364860, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-methoxycarbonyl-4H-pyrido[3,2,1-jk]carbazole-4-one (300 mg) produced in Example 176 was suspended in anhydrous methylene chloride (100 ml), and diisobutylaluminium hydride (1M solution in methylene chloride, 4.3 ml) was added dropwise to the suspension in an acetone-dry ice bath. The mixture was stirred at room temperature for 1 hour, and methanol and water was added to the reaction mixture. The floating materials formed were separated by filtration, and the filtrate was distilled under reduced pressure to remove the solvent. The residue was purified by silica gel flash column chromatography (eluent: ethyl acetate) to obtain the title compound (70 mg, 26%).

Workup

  1. customThe floating materials formed
  2. customwere separated by filtration
  3. distillationthe filtrate was distilled under reduced pressure
  4. customto remove the solvent
  5. customThe residue was purified by silica gel flash column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-f544a05f6e884c0aa4393ac70476b364
Source dataset
uspto-grants-2000_01
Patent number
US06018046

Reaction notes

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