Methyl morpholine oxide → HCID 59858030, compound

HRID 1671620Notes

Reaction equation

HRID 1671620 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 acetonitrile (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-00f43999e6ab4c46b870f69373badca5
Source dataset
uspto-grants-2011_08
Patent number
US07994326B2

Reaction notes

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