Methyl morpholine oxide → HCID 86622961, compound

HRID 1715424Notes

Reaction equation

HRID 1715424 reaction equation
C[N+]1([O-])CCOCC1.[C:9]([O:13][C:14](=[O:29])[N:15]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([CH2:27][OH:28])[CH:21]=1)[CH2:16][CH3:17])([CH3:12])([CH3:11])[CH3:10]>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[C:9]([O:13][C:14](=[O:29])[N:15]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([CH:27]=[O:28])[CH:21]=1)[CH2:16][CH3:17])([CH3:10])([CH3:11])[CH3:12]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 68504289HCID 68504289, compound

Product 1

HCID 86622961HCID 86622961, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

NMO (133 mg, 0.956 mmol) was added to a sol. of [2-(4-chloro-3-hydroxymethyl-phenyl)-ethyl]-ethyl-carbamic acid tert-butyl ester (110 mg, 0.319 mmol) in CH2Cl2 (7.0 mL). The mixture was stirred for 30 min, and tetrapropylammonium perruthenate (11.2 mg, 0.032 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 (80 mg, 80%). LC-MS: tR=1.07 min.

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-ba152b662ca845f2a724a37157120a73
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

Loading…