Methyl morpholine oxide → HCID 58986320, compound

HRID 420800Notes

Reaction equation

HRID 420800 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][O:19][CH3:20])=[CH:14][CH:15]=2)[C:10]([CH2:21][OH:22])=[C:9]1[CH:23]([CH3:25])[CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][O:19][CH3:20])=[CH:14][CH:15]=2)[C:10]([CH:21]=[O:22])=[C:9]1[CH:23]([CH3:25])[CH3:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 58986359HCID 58986359, compound2×

Product 1

HCID 58986320HCID 58986320, compound

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

General Procedure B. To a solution of (1-benzyl-2-isopropyl-5-(methoxymethoxy)-1H-indol-3-yl)methanol (Compound 3, 120 mg, 0.35 mmol) in CH2Cl2 was added 4-methylmorpholine N-oxide (NMO, 129 mg, 1.1 mmol) and tetrapropylammonium perruthenate (TPAP, 14 mg, 0.040 mmol). The reaction was stirred at room temperature for 2.5 h, and the product was purified by flash chromatography on silica gel eluting with 20% EtOAc-hexanes to yield 1-benzyl-2-isopropyl-5-(methoxymethoxy)-1H-indole-3-carboxaldehyde (Compound 4) as an off-white solid.

Workup

  1. customthe product was purified by flash chromatography on silica gel eluting with 20% EtOAc-hexanes

Sources & evidence

ORD record
ord-c8a585fcaa3942bcae6a2aa9409d988f
Source dataset
uspto-grants-2012_01
Patent number
US08097644B2

Reaction notes

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