Methyl morpholine oxide → HCID 86622957, compound

HRID 1715409Notes

Reaction equation

HRID 1715409 reaction equation
C[N+]1([O-])CCOCC1.[Cl:9][C:10]1[CH:20]=[CH:19][C:13]([CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:12][C:11]=1[CH2:21][OH:22]>CC#N.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Cl:9][C:10]1[CH:20]=[CH:19][C:13]([CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:12][C:11]=1[CH:21]=[O:22]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 67148459HCID 67148459, compound

Product 1

HCID 86622957HCID 86622957, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

NMO (1.15 g, 8.26 mmol) was added to a sol. of N-(4-chloro-3-hydroxymethyl-benzyl)-acetamide (588 mg, 2.75 mmol) in CH3CN (27 mL). The sol. was stirred for 30 min at rt, and tetrapropylammonium perruthenate (97 mg, 0.28 mmol) was added. The mixture was stirred for 1 h at rt, and was filtered over Celite. The precipitate was washed with CH3CN. The filtrate was evaporated under reduced pressure. Purification of the crude by FC (CH2Cl2/MeOH 95:5) yielded the title compound (382 mg, 66%). LC-MS: tR=0.71 min; ES+: 253.07.

Workup

  1. stirringThe mixture was stirred for 1 h at rt
  2. filtrationwas filtered over Celite
  3. washThe precipitate was washed with CH3CN
  4. customThe filtrate was evaporated under reduced pressure
  5. customPurification of the crude by FC (CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-4152bb212b024f1c900ba836a994933d
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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