Methyl morpholine oxide → HCID 59219004, compound

HRID 2247421Notes

Reaction equation

HRID 2247421 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]([O:24][CH3:25])=[C:13]([CH:23]=2)[CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:6]=[CH:7][CH:8]=1.C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH:2]([C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]([O:24][CH3:25])=[C:13]([CH:23]=2)[CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH:6]=[CH:7][CH:8]=1)=[O:1]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 22930486HCID 22930486, compound

Product 1

HCID 59219004HCID 59219004, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

747 mg of t-Butyl N-{5-[3-(hydroxymethyl)-phenyl]-2-methoxybenzyl}carbamate, 510 mg of N-methylmorpholin-N-oxide, 76 mg of tetrapropyl ammonium perruthenate and 1 g of 4A molecular sieve powder were dissolved in 1 g of dichloromethane, and the mixture was stirred at room temperature for 2hours. The reaction mixture was filtered and the filtrate was evaporated. The residue was purified by silica gel column, to give 566 mg of the title compound in the 3:1→1:1 hexane-ethyl acetate fraction.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated
  3. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-6cea4c44781c4963aaf85397d73aac56
Source dataset
uspto-grants-2010_03
Patent number
US07687664B2

Reaction notes

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