HCID 15221118, compound → HCID 18656670, compound

HRID 233790Notes

Reaction equation

HRID 233790 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][CH:3]=[N: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][CH:3]=[N:2]1

Participants

4

Reactant 1

HCID 15221118HCID 15221118, compound

Product 1

HCID 18656670HCID 18656670, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (-)(2aR,4S)-6-(5-isoxazolyl)-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole (253 mg, 0.8 mmol) and 1 g of MnO2 in 100 ml of CH2Cl2 was sonicated at 50-55 KHz for four hours. The reaction mixture was warmed to reflux during the time period. After four hours, the reaction mixture was filtered through a celite pad and the filtrate was concentrated to dryness in vacuo. The resulting residue was chromatographed (flash column, silica gel, EtOAc) to provide 130 mg of title product. Recrystallization from hexane gave 60 mg of purified title product.

Workup

  1. customwas sonicated at 50-55 KHz for four hours
  2. temperatureThe reaction mixture was 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 resulting residue was chromatographed (flash column, silica gel, EtOAc)

Sources & evidence

ORD record
ord-3277c96d7a1c4b999fdcb5d759f9c905
Source dataset
uspto-grants-1997_01
Patent number
US05594019

Reaction notes

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