HCID 18654739, compound → HCID 9949130, compound

HRID 1377812Notes

Reaction equation

HRID 1377812 reaction equation
[O:1]1[C:5]([C:6]2[CH:14]=[CH:13][C:12]3[NH:11][CH2:10][C@@H:9]4[CH2:15][C@H:16]([N:18]([CH2:22][CH2:23][CH3:24])[CH2:19][CH2:20][CH3:21])[CH2:17][C:7]=2[C:8]=34)=[CH:4][N:3]=[CH:2]1>C(Cl)Cl.O=[Mn]=O>[O:1]1[C:5]([C:6]2[CH:14]=[CH:13][C:12]3[NH:11][CH:10]=[C:9]4[CH2:15][C@H:16]([N:18]([CH2:22][CH2:23][CH3:24])[CH2:19][CH2:20][CH3:21])[CH2:17][C:7]=2[C:8]=34)=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 1

HCID 18654739HCID 18654739, compound

Product 1

HCID 9949130HCID 9949130, compoundYield 34.4%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (-)(2aR,4S)-6-(5-oxazolyl)-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole (300 mg, 0.9 mmol) and 0.5 g of MnO2 in 50 ml of methylene chloride was stirred at room temperature for 16 hours. The oxidant was removed by filtration through celite. The crude product obtained after filtering and removing the solvent was purified by flash chromatography, using ethyl acetate as eluent, to provide 100 mg of title compound. Recrystallization from hexane gave 60 mg of pure title compound.

Workup

  1. customThe oxidant was removed by filtration through celite
  2. customThe crude product obtained
  3. filtrationafter filtering
  4. customremoving the solvent
  5. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-d28b21f08187418fba2be177fd002255
Source dataset
uspto-grants-1997_09
Patent number
US05665758

Reaction notes

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