Methyl morpholine oxide → HCID 86622962, compound

HRID 2428112Notes

Reaction equation

HRID 2428112 reaction equation
C[N+]1([O-])CCOCC1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH:18][C:19](=[O:21])[CH3:20])=[CH:12][C:11]=1[CH2:22][OH:23]>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH:18][C:19](=[O:21])[CH3:20])=[CH:12][C:11]=1[CH:22]=[O:23]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 67148527HCID 67148527, compound

Product 1

HCID 86622962HCID 86622962, compoundYield 50.5%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

NMO (184 mg, 1.32 mmol) was added to a sol. of N-[2-(4-chloro-3-hydroxymethyl-phenyl)-ethyl]-acetamide (100 mg, 0.439 mmol) in CH2Cl2 (9.22 mL). The mixture was stirred for 30 min, and tetrapropylammonium perruthenate (15.5 mg, 0.044 mmol) was added. The mixture was stirred for 1 h at rt, and was filtered over celite. The filtrate was evaporated under reduced pressure. Purification of the crude by FC(CH2Cl2/MeOH 49:1) yielded the title compound (50 mg, 50%). LC-MS: tR=0.75 min; ES+: 267.10.

Workup

  1. stirringThe mixture was stirred for 1 h at rt
  2. filtrationwas filtered over celite
  3. customThe filtrate was evaporated under reduced pressure
  4. customPurification of the crude by FC(CH2Cl2/MeOH 49:1)

Sources & evidence

ORD record
ord-0dabdf7747934215a11dce75df8462b6
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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