Methyl morpholine oxide → HCID 66813007, compound

HRID 1097946Notes

Reaction equation

HRID 1097946 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:27])[CH:10]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[N:16]=[CH:15]2)[OH:11].C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:27])[C:10]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[N:16]=[CH:15]2)=[O:11]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 66813144HCID 66813144, compound

Product 1

HCID 66813007HCID 66813007, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2,4-dichloro-phenyl)-1-(1-phenyl-1H-indazol-5-yl)-propan-1-ol (180 mg) in dichloromethane (5 ml) was added powdered molecular sieve 3A (1 g). Tetrapropylammonium perruthenate (16 mg) and 4-methylmorpholine-4-oxide (106 mg) were added. The mixture was stirred at room temperature for 1.5 h. The mixture was filtered and the filtrate was concentrated to dryness. The product was purified by chromatography (SiO2, cyclohexane/EtOAc 1:0=>1:3) to give the title compound (149 mg) as an off-white solid. MS (m/e)=394.9 [M+H+].

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe product was purified by chromatography (SiO2, cyclohexane/EtOAc 1:0=>1:3)

Sources & evidence

ORD record
ord-a3a3f6ec478147d19721e2f0dd79838a
Source dataset
uspto-grants-2012_03
Patent number
US08143280B2

Reaction notes

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