Methyl morpholine oxide → HCID 86622957, compound

HRID 2428100Notes

Reaction equation

HRID 2428100 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-89cd0e6200f349a19483af2ae23d49d2
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

Loading…