Methyl morpholine oxide → HCID 66813007, compound

HRID 333845Notes

Reaction equation

HRID 333845 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-05065fa93f154d54b857afa68c0d6b6f
Source dataset
uspto-grants-2014_11
Patent number
US08883786B2

Reaction notes

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