HCID 15221115, compound → HCID 15227863, compound

HRID 2379749Notes

Reaction equation

HRID 2379749 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([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)=[N:2]1>C(Cl)Cl.O=[Mn]=O>[O:1]1[CH:5]=[CH:4][C:3]([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)=[N:2]1

Participants

4

Reactant 1

HCID 15221115HCID 15221115, compound

Product 1

HCID 15227863HCID 15227863, compoundYield 30.9%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (+)(2aS,4R)-6-(3-isoxazolyl)-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole (180 mg, 0.5 mmol) and 1 g of MnO2 in 40 mL of CH2Cl2 was sonicated at 50-55 KHz for 2 hr. The reaction mixture warmed to reflux during the time period. The reaction mixture was filtered through a celite pad and the filtrate was concentrated to dryness in vacuo. The residue was chromatographed (flash column, silica gel, ethyl acetate) to provide 50 mg of the isoxazole indole product as an oil.

Workup

  1. customwas sonicated at 50-55 KHz for 2 hr
  2. temperatureThe reaction mixture warmed
  3. temperatureto reflux during the time period
  4. filtrationThe reaction mixture was filtered through a celite pad
  5. concentrationthe filtrate was concentrated to dryness in vacuo
  6. customThe residue was chromatographed (flash column, silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-2f848309873644029695a61a48091a15
Source dataset
uspto-grants-1994_11
Patent number
US05364856

Reaction notes

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