Methyl morpholine oxide → HCID 19029351, compound

HRID 2256325Notes

Reaction equation

HRID 2256325 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:22][CH2:23][OH:24])[CH2:10][C:11]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:22][CH:23]=[O:24])[CH2:10][C:11]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 190293341-[3-(3,4-dichlorophenyl)-5-hydroxy-1-oxopentyl]-1H-indole

Product 1

HCID 19029351HCID 19029351, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-[3-(3,4-dichlorophenyl)-5-hydroxy-1-oxopentyl]-1H-indole (4.25 g) and molecular sieves (4A, 2.75 g) in CH2Cl2 (40 mL) and was treated with TPAP (50 mg) and 4-methylmorpholine-N-oxide (2.75 mg) and stirred at room temperture for 2 hours. The reaction mixture was filtered through a pad of silica gel rinsed with EtOAc (100 mL) and concentrated under reduced pressure to yield an oil. Silica gel chromatography eluting with 50-75% EtOAc/Hexanes gave the desired title compound (930 mg).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of silica gel
  2. washrinsed with EtOAc (100 mL)
  3. concentrationconcentrated under reduced pressure
  4. customto yield an oil
  5. washSilica gel chromatography eluting with 50-75% EtOAc/Hexanes

Sources & evidence

ORD record
ord-f54b58b1aadb461895977362de3caaba
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

Loading…