Methyl morpholine oxide → HCID 59858030, compound

HRID 1693344Notes

Reaction equation

HRID 1693344 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH:15]2[CH2:19][CH:18]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH:16]2[OH:28])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].C[N+]1([O-])CCOCC1>ClCCl.C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH:15]2[CH2:19][CH:18]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][C:16]2=[O:28])[N:9]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 2

HCID 82029Methyl morpholine oxideHCID 67280696HCID 67280696, compound

Product 1

HCID 59858030HCID 59858030, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Tetrapropylammonium perruthenate (0.07 mmol, 5 mol %) was added to a stirred solution of [6-(4-tert-butoxycarbonylamino-2-hydroxy-cyclopentylmethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester IV-3 (0.14 mmol) and N-methylmorpholine-N-oxide (0.26 mmol) in dichloromethane (9 mL) and acteonitrile (1 mL) at room temperature, and was allowed to react overnight. When complete, the solvent was evaporated in vacuo and the residue was purified by column chromatography (silica gel, CH2Cl2:EtOAc, 8:2) to afford pure product as a white solid (67%).

Workup

  1. customat room temperature
  2. customto react overnight
  3. customWhen complete, the solvent was evaporated in vacuo
  4. customthe residue was purified by column chromatography (silica gel, CH2Cl2:EtOAc, 8:2)

Sources & evidence

ORD record
ord-df33a824c2d3414b9c9aa74b1767f87f
Source dataset
uspto-grants-2012_04
Patent number
US08158658B2

Reaction notes

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